He’s got a new book coming out, titled Dirtbag Rich, in which I play a very minor role, based on a convo we had on his podcast last year.

He pitched me on writing an essay for the newsletter and said, send me what ya got. I liked it. Especially this frame:

Where are the people who have found ample time, money, and purpose in their 20s, 30s, and 40s? What about those with children? What about those who don’t particularly love dirt? What about those with difficult upbringings, or constant anxiety, or, or, or… The stories are all there.

I also just love the title Dirtbag Rich pairing. It might be better than Pathless Path. The combo of “dirtbag,” a term often embraced by climbers who build their lives around bare minimum living, with rich, is nice.

Without further ado…

Time, money, and purpose

If you’re a Paul Millerd fan, I suspect you already think differently about time, money, and purpose.

Time: You try hard to remain in control of the hours of your day, week, and year. Perhaps you work regularly but part-time, intensely but seasonally, or possess an otherwise normal job that allows significant breaks. The time of your life does not belong to your employer, your clients, or anyone else—it is yours alone.

Money: You attempt to earn a substantial amount relative to your efforts, perhaps via a high hourly wage, big payouts after big gigs, or some version of (so-called) passive income. Paired with low expenses, you can subsist happily on a lower income—sometimes even “poverty wages”—and enjoy the spacious freedom necessary to do what you love.

Purpose: You really, truly attempt to “do what you love,” right here, right now, in your one life on Earth. Instead of making purpose wait for the weekend, you actively seek it, compensated or not, day in and day out. Because why else would you so carefully manage your time and money? What would be the point?

While the status quo tells you to earn money at the expense of time and purpose—two resources you’re supposedly meant to reclaim in retirement (a.k.a. the pre-death siesta)—you have resolved to take a different approach.

Some call this the pathless path, a label I quite enjoy.

For me, another term fits even better: dirtbag rich.

What’s a dirtbag?

The first dirtbags were hardcore rock climbers in Yosemite Valley who camped illegally, showered infrequently, and scavenged for meals. When they needed money, they’d leave the Valley to paint houses, wait tables, teach skiing, or even take a desk job: anything to refill their coffers and get back to the big walls. They lived like bums in pursuit of the good life.

Today dirtbags come in many flavors, not just “climber” and “white male.” Some are trail runners, mountain bikers, long-distance hikers, backcountry skiers, cross-country cyclists, or endless-summer surfers. Others are dancers, slackliners, or perpetual travelers. All are passionate. All are extreme. None are what the mainstream would describe as “balanced.”

Some dirtbags live in vans, trucks, or tents. Others couchsurf, hitchhike, or stay with friends. Some do pay rent: just not very much, and not for very long. For dirtbags, full-time, full-price rental contracts lie somewhere between a luxury and an obscenity.

Many dirtbags come from middle-class security. Some come from upper-class privilege. Others come from next to nothing.

All dirtbags revere nature, movement, and thrift. All struggle to fit into conventional society. All want to be left alone to do what they love, while they also yearn for membership in a tight-knit community of the similarly obsessed.

Many who lead such lives aren’t aware of the label “dirtbag.” Of those who are aware, many don’t welcome its associations. I understand their aversion, but I like the term.

To me, being a dirtbag simply means that you’re too busy following your bliss to worry about a little dirt under your nails. It means you’re doing something right.

Freedom = moving your body swiftly through nature

As I recount in my new book, Dirtbag Rich: High Freedom, Low Income, Deep Purpose, I never made a very good dirtbag.

My attempt to hike the Pacific Crest Trail at age 22 ended two weeks after it started, catapulting me into a multi-year crisis of commitment. I failed to live happily outdoors like a “real” dirtbag, yet I was also incapable of holding a “real” job like a normal member of society.

Three months of soul-seeking in South America revealed the first glimpses of an answer: I needed to take the middle path. I needed to craft a new way of living in the liminal space between hardcore dirtbagging and conventional wealth-seeking.

Because the truth was: I loved sleeping in the dirt, in a bag. I loved it when I was 22, and today at 43, I still do. Living like a hobo in the mountains is one of my “peak experiences,” and that’s not going to change.

Anytime I move my body swiftly through nature, in fact—whether backpacking, day hiking, trail running, bicycle touring, or swimming in alpine lakes—everything tastes, smells, sounds, and feels more intense. The same goes for international travel. Whenever I’m in motion, I remember more details, and everything feels more “real.” Daily life in cities, in contrast, is too easily forgettable and “unreal” (with the exception of social partner dancing: the one thing that keeps me circling back to big cities).

If you’re anything like me, then you, too, face a series of dilemmas:

• You derive profound purpose from moving your body through nature, yet you’re not ready to live like a total dirtbag.

• You won’t be a mere weekend warrior, nor will you drop out of polite society.

• You crave wilderness immersion, long-term travel, retreats with friends, and other transformative experiences, while also desiring to put something away for the future.

You are an irrational, implacable, exuberant creature who wants it all—time, money, and purpose—with very few compromises. Heaven help you.

Impossible contradictions are fun

As I navigated these tensions throughout my twenties and early thirties, many questions remained. How could I earn enough while only working part-time? How would I manage without a home base? What if I wanted a family? And beneath them all: What if I was making a giant, life-shattering mistake by not swallowing my discomfort, burying these impossible desires, and getting on with a normal existence?

I knew that every path has trade-offs. If I lived for adventure, I might not have kids. If I had kids, I’d certainly take fewer adventures. Travel would change me, just as rootedness would change me. Working for myself might be the best thing I ever do, and turning my passion into a business might suffocate it.

No one can have it all. But maybe, just maybe, I could have more than the world promised.

And—spoiler alert!—I have.

I ended up creating a little travel company for unschooled teenagers: one that let me share my love of travel and nature with delightful young people while also earning decently in a brief period. I dedicated my newfound free time to nature, dance, travel, adventure, and writing books about self-directed learning. I did not start a family, but I did develop deep friendships across the world and find profound meaning in playing a unique role in the lives of other people’s children.

Attempting to live dirtbag rich means navigating a series of seemingly impossible contradictions. Some of these contradictions are very real—like balancing freedom and romantic attachment—while others are but smoke and mirrors. As with any serious attempt to live differently, fear of the unknown stops most from ever trying. Nor is it a mere privilege issue, as wealthy people are often the most chained to convention; the ideal setup may be moderate privilege + high idealism.

Yes, it’s possible. Yes, it’s hard. On any pathless path, it’s a question of what kind of glory you crave and what kind of difficulties you can face down.

How (and where) to begin

Ask yourself that age-old question: “If I suddenly had [ridiculous sum of money] in the bank, how would I live differently?”

If the answer is “not much differently”—if you’d reduce your working hours a bit, for example, but not change your work—then you’ve already struck a magical balance of time, money, and purpose. Keep it up!

If the answer is “VERY, VERY DIFFERENTLY”—if you’d pursue a whole new vocation or wander in the woods indefinitely—this indicates a need for change, and a possible new direction for your life.

There’s no silver bullet for this kind of stuff; distrust anyone who insists otherwise. Rather, you need a wealth of examples.

This is what Paul has achieved with his books and the Pathless Path Community, and it’s what I’m attempting with my dirtbag rich interview series (which includes Paul). Where are the people who have found ample time, money, and purpose in their 20s, 30s, and 40s? What about those with children? What about those who don’t particularly love dirt? What about those with difficult upbringings, or constant anxiety, or, or, or… The stories are all there.

To begin living differently, you need a bunch of role models. None will exactly match your background, values, risk tolerance, or other constraints. Each will have something to teach you. Listen to their stories: the long version, not the soundbyte. When one resonates, reach out and ask a few follow-up questions, as a 22-year-old adventurer from Chicago did with me yesterday. (Remember the promise of the early internet: You can just find interesting people and connect directly with them!)

This is how any pathless path—or dirtbag rich life—begins and evolves. Watching, thinking, feeling, researching. Getting honest, getting vulnerable, getting in touch. And at some point: making a big move. What that specific move is, I cannot say. All I know for sure is that at some point, you must stop gathering data—and act.

As for me, I’m going to keep dancing, cycle touring, working with unschooled teenagers, and losing myself in the wild places of the world. I’ll keep visiting friends and family, showing up for other people’s kids, writing for a small but engaged audience, and remaining open to the possibility of another big pivot.

This is a life I wouldn’t dream of trading away for a pile of money, the myth of retirement, or some other distraction. It’s far from perfect, it’s still fraught with uncertainty, and it could all end tomorrow. But we’re not here to win the game of life—we’re here to play progressively more interesting levels. Onwards.𖤓

It’s Paul Again. If you want to check out his book, it’s $4.99 on Kindle or on his website. I already grabbed one.

This is the longest break I’ve taken from writing this newsletter since the birth of my daughter three years ago. It wasn’t the contemplative kind of break I would often take early in my journey, but it was still refreshing. It was a useful practice to take a step back and assess all the various projects I’m involved in and figure out where I should be spending my time in the future.

This mini-sabbatical also coincided with a few other big life events.

First, I’m participating in a five-month experimental travel group called the traveling village.

We are in the second location, in Taiwan, and have really enjoyed the experience so far. We spent the first five weeks in Vietnam and it’s been a possibility-expanding trip. The payoff to having other families who are location-independent around is pretty amazing, it’s something we’ve been missing for a couple of years. Right now, we’re living with another family in the same house with a four- and six-year-old overlooking the ocean, with nine other families within a three minute walk. It’s convinced me that hyper co-location is a cheat code for taking the stress away from having young kids. It turns out the “village” idea basically works, it just takes quite a bit to get others onboard.

More thoughts on this soon but please send me questions.

Second, book, Made in Taiwan, was released in traditional Chinese in Taiwan last week.

This has been a huge project for her, and I can say with complete confidence that I think she nailed it. With the help of AI translation tools, I was lucky to be able to collaborate with her on the developmental editing. This was certainly a challenge as I probably pushed her a bit too hard at points, but every time I did, she would come back with a rewrite that blew me away. I am lucky to be married to Angie and am always amazed at how she continues to grow and never gives up despite the challenges she faces. We are currently working together on an English translation too, which will come out later this year.

In the meantime, you can grab a copy to gift to the person in your life that reads traditional Chinese. Or, you know, you can buy it too, because there are no laws against you buying a book you can’t read:

Grab The Chinese Version

Finally, we have to talk about Claude Code.

Right before I took this little break, I had a call with , a fellow tinkerer and writer I’ve known since the dog days of the pandemic. The call we had was mind-blowing and I especially appreciated how Alex is approaching using the tool as a creator-first, not as a hustle bro telling everyone “you’re already late.”

This is an unsolicited ad for Alex’s resources on codeforcreatives.com - Alex is a genuinely nice and generous person and creative force and excellent writer. It’s been cool to see him find his thing and be so excited about this, so go there and support him or set up a call if you want to be Claude Code pilled.

I had dabbled with Cursor and Claude Code a bit last year but they never worked and I’d always face too many roadblocks to executing any of the projects I’ve wanted to work on.

But this time really is different. With the new models and UX upgrades, Claude Code, whether in the app or command line, is one of the most powerful tools I’ve ever used. In increasing leaps of boldness, I’ve passively executed on a number of projects in some of the free time I had due to the the efficiencies of scale of traveling with many other families whose kids want to play with my daughter:

#1 A health dashboard: I have a folder of my lifetime health records, and for the first time, Claude was able to easily build me a custom dashboard where I can notice issues, and also brainstorm any problems I’m having based on all this information as context. I suspect everyone will have something like this within a year or two.

#2 Blog Rebuilds: Completely transferred three of my sites, pmillerd.com, angiecreates.io, and strategyu.co, to a static site, each in about 4-5 hours of work: I published a skill on my process here.

#3 Teachable Clone: After doing StrategyU blog rebuild, I started thinking: could I replace Teachable, which was hosting my online course? Part of the reason I wanted to attempt this was that the platform literally hadn’t made any meaningful upgrades in years, and the tracking I was doing for ads didn’t work at all anymore. In less than ten days, I went from tweet to launch.

The final stack was mostly free dev tools: Next, React, Typescript, Convex, Mux, Posthog, Resend + Stripe. It sounds complex but for someone who’s been dancing around these tools for years but could never quite do anything meaningful, it all sort of clicked and fell into place. I just migrated all users and downgraded my Teachable subscription yesterday.

#4 Publishing Chinese EPUBs and Print Books: Angie is self-publishing her book in Taiwan. We have a partner helping with print distribution in Taiwan but had to setup the EPUB and print-on-demand versions everywhere else. This was much more challenging than I expected because Traditional Chinese is typically read right to left, top to bottom. A typical page looks like this:

It turns out that the support for this style EPUB is not very widespread and many books in Taiwan don’t even do it because of technical limitations!

Claude Code to the rescue. Over a couple of weeks I was able to:

• Reformat a beautiful EPUB as seen above, 100% via code, keeping the original text intact as well, including custom versions for Apple, Kobo, and Readmoo.

• Produce a .docx version for Amazon Kindle, as they don’t support vertical Chinese yet, and

• I was able to solve 3-4 gnarly PDF issues on documents we needed to submit for print-on-demand to IngramSpark and Lulu

The crazy thing about these things is that in the past they would all require specialized paid contractors to execute. I estimate we likely saved $1000-$2000 by doing all these things on our own (not to mention made a better product).

#5 Then, I shipped a website in Chinese without fully knowing the language, all via Claude Code, building out a bunch of cool features, like automated testimonials and a smooth process for digital book gifting based on a code.

#6 Finally, a fun experiment, an agentic Store for My Books: Half-joking, half-serious, I decided to launch a store for agents to buy my book:

Anthropic is supposedly going to pay out $3,000 per book that they pirated, so I want to make sure these big labs have the chance to grab my book for a little cheaper:

It’s clearly the way the web is going, designing interfaces, APIs and processes that enable agents to interact with your products and work. Shopify has recently just made agentic shopping a live feature in the last week. So all you need to do is tell your agent to come to my site and follow the simple instructions:

Browse the catalog at https://agent.pathlesspublishing.com/api/catalog

To purchase, POST to https://agent.pathlesspublishing.com/api/purchase with:
{
  “slug”: “the-pathless-path”,
  “email”: “YOUR_EMAIL”,
  “buyerType”: “personal”
}

This returns a Stripe checkout URL. Open it to complete payment.

When the purchase is made, it automatically injects a license and hash in the EPUB, MD, and JSON files with terms and specific instructions on how to use the book and how to source it (encouraged).

While this was a fun little experiment (it took 3 hours to code up) it made me realize that there is probably a lot more potential in publishing to build a new stack for selling books, especially for indies like me who won’t be slowed down by traditional publishers. This also makes me incredibly bullish on digital formats of books, mostly because they will be easier to acquire and self-DRM tools will be easier than ever to use. Likely more on this throughout the year

I’m feeling very energized

While it looks like I was working a lot, it really didn’t feel like that. Most of the above projects with Claude Code did NOT take much focused energy. I dabbled on them here and there, during naps, at night, and in 2 or 3 focused work sessions. It certainly required strong basic foundational knowledge of the various tools I was using, but that is something I had in spades after years of tinkering and having fun online.

For someone like me, who doesn’t want to grind my way to success, these tools are incredibly powerful. They remove so much friction and annoyance from launching digital experiments, sites, and products, that I’m rethinking many of the things I thought I’d never do. On top of that, I’m really thinking deeply about what work means in this new reality. This way of working is definitely going to change knowledge work, but I need to think a bit more about it.

Personally, my mind is overflowing with ideas and feeling more open and excited than I have been in a while.

Do sabbaticals always work this way? Aligning with what the universe is ready to tell you? It certainly seems like that sometimes and based on what many of you have shared, it does..

With the publication of Angie’s book it also feels like a new chapter is finally starting.

The past two years have been incredibly hard for me. I’ve been doing a lot of childcare, by choice, and really been enjoying it. But man oh man, has it been a growth experience. I’ve had to grow emotionally, learn how to ask for what I need in my relationship, and also learn to feel the feelings that are easy to suppress when you are trying to hold it together for everyone else.

Angie’s book was something I really believed in and felt was an important core project for our family, despite it being something that may not bring financial rewards. I am glad we oriented our family and life around it. Taking a step back from my work since Good Work was published in October 2024 has been an interesting experience. I’ve definitely found the limit of not enough work and it’s cemented my belief that the right amount of childcare for a parent is not 100% and the right amount of work is not 0% either. The balance is somewhere in the middle.

Through the traveling village, a year of nomadic living, working closely with Angie on a creative project, stepping up as a dad, and growing as a family, I am starting to feel more confident about how the next chapter of our life may unfold.

But as always, it is exactly that, an unfolding.

But after this break, I actually feel like I'm letting things unfold again rather than trying to take off the wrapper by force.

That’s it for today and I’m incredibly grateful for you all.

Keep dreaming big, taking chances, and moving toward the life that matters to you.

See you soon.

-Paul

P.S. I have been having a lot of issues with Substack delivery over the last six months, and I’ve been having large unexpected unsubscribes after sending each issue. It’s been weird, though I may have found the source of the issue. I had my subdomain for substack “proxied” on my DNS which Claude tells me might have flagged my domain for months. If you have had any issues receiving my email or are seeing this one for the first time in a while, let me know. Hopefully everything is fixed now.

Yo.

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

A couple quick shouts:

• is publishing her book Made in Taiwan in Traditional Chinese next week! The final product is incredible; it’s one of the best memoirs I’ve read (I am biased, but I think I will be quickly validated by readers!). We’re excited to share it in English after we co-translate it later this year, so stay tuned. If you read Chinese or would like to grab a copy to support her, all the links are here: Made in Taiwan.

• You can now purchase notebooks, shirts, my paperbacks, and Angie’s books all directly from my Shopify store.

Below is a guest post/Q&A from Holly Gabrielle, who recently left the creator world to go all in on trying to become a top Hyrox athlete. I love highlighting new paths that exist in the world, and this one definitely qualifies.

Ok, you just quit your job, which was working on Ali Abdaal’s team, after reading Good Work. What is going on over there? Is Ali getting ready to ban my books?

Haha, to be fair, Ali might think twice about giving out free copies of Good Work to members of his team in future. But my departure was the least dramatic thing ever - I simply sent a Slack message to Angus (Ali’s general manager) basically explaining that I wanted to go off and do my own thing … or in other words, quit a perfectly stable copywriting job to chase a dream of becoming one of the top 15 women in the world at a sport I’d never actually competed in yet 😅

Absurdity aside, being part of the Ali Abdaal team is honestly so dangerous because you start believing you can do things, and I wasn’t even a full-time team member - I was freelance, working 3 days a week - yet I still caught on.

Like many of us, I was guilty of procrastinating on ideas, shutting them down, telling myself I wasn’t good enough, or just learning more and more information, convinced that I just wasn’t ready yet. But Ali talks so much about taking action and not letting your emotions or fears hold you back - whether it’s starting a YouTube channel or a lifestyle business or even something as small and personal as going on your first date - and when you work for him, it’s pretty hard not to eventually listen.

So, like many other team members, after 2 years working with Ali, I’d heard enough. I took his advice a bit too literally and decided to go all-in on trying to become an elite Hyrox athlete (and simultaneously return to my content creator origins).

You’re going to pursue being an “elite athlete”? That sounds awesome. I suspect needing more time for training, rest, and recovery is part of it, and a job doesn’t help with focusing on that. Any other reasons?

Yep, you’re pretty much spot on. Time for training and recovery was a huge factor, and I’m hoping this allows me to make much faster progress. But it wasn’t just about the physical time - it was a mental energy thing too.

Realistically, I could’ve kept my writing job with Ali and also gone all-in on this lofty (and pretty scary!!) goal of becoming an elite athlete. Besides, working with the team was such a great experience - the flexibility was incredible, I was always learning new nuggets of information, and the people were amazing.

But I know myself well enough to know that my brain doesn’t really switch off - and that comes at a cost.

Even though the team never gave me any super strict deadlines, I’d always push myself to write one more email before 5pm, shorten my breaks to cram in a bit more work, or find a way to level-up in my role. It was exhausting.

And it wasn’t until I came across ideas like essentialism and the “Hell Yeah or No” framework by Derek Siver (again, all through Ali) that I started to question how much of a toll it was taking on me. I also realised that it was stealing a lot of mental energy away from my runs and workouts. I’d often blindly go into a session and wonder why it felt hard. I left no time to reflect on my sessions, properly plan my workouts, or even just celebrate my small wins.

So long story short: I finally decided to step back. Yes, it’s probably been one of the hardest things I’ve ever done because saying no or quitting doesn’t come naturally to me, but I’m excited by the challenge of finally doing less to hopefully get more out of the things that mean the most to me and have the potential to completely change my life.

Are you already making money from your athletic pursuits (career, path, passion, what else do you call this?!), and how did this impact your decision?

I’d love to say yes, but the answer is no, sadly 🙈 Right now, I’m not making any money from this.

Just for some context: I’ve been “influencing” for about 10 years now. I started my first YouTube channel when I was at uni, and ever since graduating, I’ve pretty much been documenting my entire life on the internet. As a result, I have a couple of affiliate links that are earning me a bit of money right now, as well as some passive income from my old YouTube videos … but we’re talking a few hundred pounds a month.

Plus, they’re not exactly aligned with my version of good work going forwards.

Ideally, I’d love to be a full-time sponsored athlete one day - that would be absolutely unreal. And alongside that, I’m rebuilding my personal brand from the ground up.

I’ve recently started a joint YouTube channel with my partner, Angelo, where we’re documenting our journey to the Elite 15 in Hyrox, and I’m rebranding my Instagram content to be specifically within this niche. The goal is to make this financially sustainable long-term, but right now, the income from all of that is pretty much zero.

Don’t get me wrong, it’s scary not having a monthly income right now - like really scary. It was also a pretty big concern of my parents when I left my job, but I’m proud of myself for not letting financial worries stop me from going after some big goals that genuinely excite me.

What is the link between training, sharing your journey online, and how those have evolved together over time?

Love this question… although the answer isn’t super straightforward.

If we go way back, I grew up dancing competitively and have always been super interested in my own health and fitness. In all honesty, I always thought I’d live my life as a professional dancer, just like my mum, but I guess things didn’t work out that way oops - ended up going down a completely different path and studying biology at Cambridge instead.

This is when I started my first YouTube channel (2016), and even though my vlogs were heavily centred around my chaotic student life and studies at Cambridge, food and fitness were always underlying themes.

Sadly though, I experienced some pretty deep and chronic mental health issues that lasted pretty much the entirety of my teenage years and early twenties, which turned my love for fitness into something pretty toxic. I was in denial for years, and this made it really hard to be vocal about health and fitness online, because deep down I had my own things to fix first.

At the start of 2025, I stepped back from YouTube and social media a bit and decided to work on myself - focus on my writing job with Ali, spend more time with the people that matter most to me, and finally fix my relationship with food and exercise. When I could finally see how damaging this dynamic was, I thought it was best to never mention it online ever again. But I missed sharing my journey, and it’s always been something I loved.

So towards the end of the year, I thought about seriously rebranding my content. I started sharing my genuine love for food and fitness but framed it in a completely different, healthier way, and this was around the time when I’d just discovered Hyrox.

A lot of people knew I was into running and marathons, but what really drew me to this sport was that I could build my body in a way that felt most natural to me - develop strength in both my upper and lower body without having to drop weight, lose my period, or risk the injuries that often come with trying to reach elite marathon times. Training for Hyrox lets me be strong and fast, not one at the expense of the other, and I was super excited to share this with others.

Don’t get me wrong, rebranding online isn’t easy 😬 But so far, I’m having the best time sharing my fitness journey and everything I’m learning. Plus, when I announced my big goal to become an Elite 15 Hyrox athlete on Instagram recently, the response was genuinely overwhelming in the best way possible - something I really didn’t expect.

(Here’s the post if you want to check it out.)

You told me you are excited and scared to make this leap. That resonates so much. Tell me about that tension?

I’m incredibly excited because the upsides are pretty much limitless. I have no idea where this path will take me, how far I can take my fitness in Hyrox, or where I’ll be in say 3-5 years’ time.

But that uncertainty is what also makes me somewhat scared. What if things don’t work out? What if my savings dry up and I’m not yet making any money to support my life? What if I get a major injury? What if I don’t make as much progress as I think?

I can often think very catastrophically and worry too much about the “what ifs” so I’m working on trying to limit these thoughts and feelings. I’m also trying to turn these negatives into something more hopeful. In particular, I’m reminding myself that any failures are simply learnings. Even if I don’t make the Elite 15, I’ll have spent years doing something I genuinely love, becoming the strongest and healthiest version of myself, and living a life designed around my values rather than someone else’s - and to me, that’s totally worth the risk.

How much of a role was your partner deciding to quit with you in deciding to take this leap? How did you talk about the tradeoffs in the decision?

Funny story here actually: Angelo and I met on Hinge (2022) after he stumbled across one of my photos from my first ever London Marathon. We clicked pretty much straight away, and in particular, we both shared this huge love for running, fitness, and becoming the healthiest versions of ourselves.

Fast forward to 2025 and we bought a flat together in London. It was something we’d been wanting to do for a while, and we honestly thought we’d “made it” as real adults. We both had stable jobs, stable incomes, and started building the routines that we’d always talked about - run at optimal times in nice parks, go to the gym, meal prep on Sundays, stuff like that.

We genuinely thought this was it. So it makes me laugh now that only 8 months later we were looking for tenants, purchasing a 150L backpack, and getting ready to leave the country altogether 😂

I know a lot of people think we’re absolutely crazy. Like, why the hell would we give up decent jobs, a mortgage, and a life we’d spent years working towards? It just doesn’t seem to make sense.

But the thing is, sometimes you have to walk through one door in life to realise it’s not quite right for you. Sure, it would’ve been great to realise that we wanted to become elite athletes before we bought a property, but life doesn’t quite work like that.

And I guess the question is: what actually changed? And why did we change our minds?

Well, when Angelo and I started living together, we started watching more and more content online about this new and interesting sport called Hyrox. We watched races, got completely hooked, and of course, almost immediately signed up to our first one. As we were putting more and more hours into our training, we started to realise we were capped. We were working out too late, eating even later, missing sleep, recovery was suffering … and we started craving more and more time for this one thing we loved most.

At the same time, Ali was talking more and more about financial freedom and building a lifestyle business, and as his copywriter, I was literally absorbing everything he was saying and learning. Oh and I also read your book, Good Work, which made me see work in a completely new light.

So one day - I can’t remember when exactly - we dabbled with the idea of dedicating our lives to fitness. We thought about starting a business, coaching, or building an app, but then we were eventually like, why don’t we prioritise our own fitness first and then document the journey?

I’ll be totally honest here and say we hadn’t even done our first Hyrox race yet, which definitely makes us crazy, but we were so determined that with hard work and consistency, we could get to the top. And I guess only time (and a lot of hard work and sweat) will tell.

But we’re on this journey together, we have each other’s backs, and it’s the most incredible thing to be chasing your dreams with your best friend and the person you love.

What’s the plan? Where can we follow you?

Right now, the plan is to really dial in my own training and aim for the Elite 15 in Hyrox. Simple on paper, but most likely a lot harder in practice 😅

That’s my ultimate goal, but even if I don’t ever end up “making it”, I’m trying to build something sustainable alongside - long-term athlete or brand partnerships, potentially coaching if that feels like “good work” to me, and content creation that actually aligns with what I love. My athletic performance is definitely going to be the foundation, but there’s a whole ecosystem I can build around it and that’s what makes this whole thing feel less risky.

I’m currently sharing my journey, tips, and advice over on Instagram (@byhollygabrielle) where I’m active most days, and Angelo and I have started a new YouTube channel together (@angeloandholly). We’re posting one video a week to share our training, racing, and the reality of this whole journey.

Oh and we’re also travelling around and living in more affordable cities compared to London to make our savings go a little bit further. I always thought I’d be a “home” person who loves stability, but I actually don’t. I love the idea of exploring new places and building homes across the world, and I feel super lucky to do this.

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

If you haven’t filled out the reader survey, that would be a huge help:

Start Survey

(or survey here if you don’t have a Substack account)

I really enjoyed ’s book Unhinged Habits, and I’m happily writing a short post to promote it.

Too many books in this space are trying to be Deep Work or Atomic Habits. Despite using “habits,” I am grateful he did not attempt that playbook.

Some quick thoughts:

1. It was refreshingly honest: he keeps telling the reader about his experiments, successes, and failures in a down-to-earth, honest way. He didn’t seem to make any attempt at “selling” his own journey or story to make himself look impressive, nor did he try to package his life reflections into a neat framework. I liked it.

2. He shares unique perspectives and ideas he has actually tested and used in his life. Like me, he’s done many time-consuming and costly experiments on how he’s living his life. He’s made many mistakes. But that also makes his approaches useful because they are working. His 8:4 seasonal on-season/off-season approach is my favorite idea from the book (more on this below).

3. He shows the tradeoffs: Most “be successful” books are not that useful once you’ve read a few. Tactics are easy to figure out. But the tradeoffs? That’s where all the interesting ideas about the art of living are found. He has young children and other interests and preferences that take him away from work and success at this point in his journey. People may dismiss him because he’s already “made it” to some degree, but that didn’t bother me at all. Most of the interesting tradeoffs are not about money at a certain point. They are about deeper human desires like belonging, identity, and dignity. I connected with his journey of grappling with these.

4. Real personal stories: He weaved in two personal stories uniquely, as interludes to the chapters, that worked incredibly well. This made the book for me because when I finished it was like I read a good book, not just some playbook I had to feel guilty about not implementing.

YMMV, but if you liked The Pathless Path, you’ll likely enjoy this one too.

My high-level take on the book: I think Jonathan did a great job questioning the assumptions of the productivity/hustle complex and actually shows how he’s transcended many of those dynamics in his own life. Jonathan has been semi-nomadic with a family for many years and has also done the author/creator/entrepreneur thing for longer than me so the book was especially useful for me in terms of questioning and challenging a lot of my own ideas. 

The book took a little to get into, but I ended up finishing it quickly after getting into a flow. The book had its own unique structure which was really well executed with several personal interludes that made the story much more than a traditional self-help book.

Here are two ideas I’ve been thinking a lot about since:

Idea #1: The value of highly inefficient life tinkering

There’s a part where Jonathan talks about outsourcing the work to buying a bike. It’s not a major priority for him, so he lets someone else decide on the bike for him. I was expecting it to go smoothly and for him to espouse the benefits of optimizing your time. But then, he says, “the bike sucked.”

It made me laugh because I am constantly running similar experiments, often resulting in wasted time and money or finding myself in situations with unforeseen downsides.

I’ve come to see these experiences as a blessing. Earlier in my life, I was surface-level efficient, trying to manage the world. I avoided moving in uncomfortable directions because it was easier on a day-to-day basis. Now I know that the right amount of discomfort is not zero. I build inefficiency into my life. While sometimes it is annoying, it helps me be more effective in terms of constantly aligning and moving toward the life I actually want.

From Jonathan:

“There’s this old saying that goes “the unlived life is not worth living.” Well, an overly productive life is not worth living, either. But the unbalanced life . . . the 8:4 life . . . is absolutely worth living. Because the unbalanced life is full of meaningful work, serendipity, exploration, and wonder.”

I agree.

Idea #2 The 8:4 season/off-season approach

My favorite part of the book was his 8:4 framework for seasonal living. He takes 8 months of the year when he’s “on season” and then four months when he’s in an “off season.” For him, his off-season is when he and his family live abroad, homeschool their kids, and spend more time as a family.

This is something I’ve been thinking a lot about since becoming a parent: Is there a way to live seasonally like this instead of trying to have it all? When I try to be excellent at work, parenting, health, and my relationships at the same time, I end up feeling like I’m dropping the ball on everything.

I’ve been thinking a lot about moving toward a more seasonal approach while my daughter is young, and the book was helpful, mostly because Jonathan has been A/B testing this for years.

Here’s an example when he’s in writing mode:

I’m in a season of writing. It’s three months long. I hope to mostly fin-ish the first draft of this book.

⁠⁠Four mornings a week, I wake up early to write for two hours. Before bed, I review my notes and plan the next day’s writing. Three days a week (Mondays, Thursdays, and Fridays) my entire work day is dedicated to this book. I have no meetings, no phone calls, and I don’t respond to emails.

When he’s in an off season, he creates a checklist of maintenance tasks he needs to keep up with. For example, shipping a newsletter once a week, doing financial reports, fitness, and payroll for his team.

For some reason, this reframing around “maintenance tasks” really clicked for me. It made me realize that I’ve kind of been in a never-ending offseason, always in maintenance mode, never really designing any “on-season” periods.

Inspired by the book, I decided to formally embrace off-season mode and take a more formal work sabbatical from January 15th to March 1st.

One thing the book spurred me to do was an audit of my “projects” in progress, and seeing it visually confirmed how many things I’m passively managing.

I started charting out a plan for this mini-sabbatical:

For this upcoming period, I drafted some very clear priorities:

Off-season priorities:

• Enjoy the traveling village community and time with Angie and my daughter

• Trying to experiment with dealing with some long-term health issues that are lingering

Off-season maintenance tasks:

• Check email once or twice a week in a dedicated block of time

• Help Angie with any tasks needed to help launch her book in March

• (Optional): Publish guest posts from others if needed

• Reply to the one contractor helping me with a small project as needed

At the end, I’ll start adding things back, reflect on what I’ve learned, and start tinkering (inefficiently, of course) with what a more seasonal approach to life might look like.

For me, this sabbatical is exciting. It’s also me walking the walk of my own advice, I often give of “doing less on the problem.”

I may post some guest posts people are working on (submissions of fully finished posts are welcome) or a quick reflection on the traveling village, but otherwise, see you in March!

Free Copies of Unhinged Habits - I’m doing a drawing and giving away copies of Unhinged Habits in my community. If you are in there, check out the WhatsApp community announcements for the link.

Check out the book

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

If you haven’t filled out the reader survey, that would be a huge help:

Start Survey

(or survey here if you don’t have a Substack account)

A reader sent me these questions and gave me permission to share them

Reader is a 25-years old who has always been a winner on her default path. Working on Wall Street but feeling deeply unfulfilled and thinking about exploring a career break.

#1 Have you ever regretted not stepping onto the pathless path earlier than you did? As someone who just turned 25 and only had 3.5 years of experience working full-time in a big global company, I wonder if this is too early for me to go on this path.

It’s so hard to actually consider rewinding the clock. I think I wish I had stayed at McKinsey longer. To me, it was a mistake to leave so quickly to go get an MBA when I was 25. That was pure prestige goggles, and the just a general restlessness to keep moving. It was such a great place to work, and I had a clear path with supportive managers to move into more challenging roles. I also had many good friends there. ‘

I got swept up in everyone around me applying for MBA and other grad programs. I think for me, a big part of this was just scarcity mindsey. I felt like I had snuck into McKinsey and wasn’t like the other people working there. I had an urgency to capitalize on my opportunities.

But by doing this, I ended up sort of adrift for the next 7 years, bouncing from one consulting firm to another. Also, that clear path for growth never happened again. I had an absurdly bad stretch of bad luck, ending up in three consecutive positions where the senior person in my department quit before I started.

In my final job, I worked with a partner who really challenged me and pushed me to work more independently and directly with clients. I gained a lot of confidence in that role, and it helped me feel like I could sell freelance projects on my own but that job had a lot of other issues, and I probably led to a lot of burnout and resentment that I spent years recovering from.

Despite these missteps, I was still learning a bunch of random things by moving jobs, shifting my focus over time, learning on my own, and doing stuff beyond work. Even though I certainly still learn and grow on my own, I do sometimes miss the structure of a workweek, deliverables, and good teammates pushing me to do better.

But the regret is less about staying so long and more that I stayed too long on a path with clearly declining motivation over time. Jumping from job to job helped increase short-run motivation and learning every time I leapt, but the trend was not in a good direction.

So the question is instead: Are you in the flow of tasks and activities where your energy and interest level are at least steady or growing? If not, what actions might you have to take to move closer to such a path?

It might be worth thinking less in years before you are “ready” than looking at the next job/gig/step as one that hopefully pushes you and challenges you in a way you are already wanting to get better. What are the jobs, places, or gigs you could pursue that would increase your odds of being on a path where you are progressing in the way you want to progress? I think there are many new kinds of jobs in this emergent hybrid economy between normal jobs and the creator economy that are really great places to work. Working for top creators, talent agencies, in social media, and startups can give you access to feedback on increasingly valuable skills.

I think stepping back, you likely need some story to make sense of it, and also some sense of what you are hoping to gain. I’ve called this “leap capital” recently, or the story you are telling yourself that helps you make sense of your transition. Is it a “one-year experiment” or is it a permanent leap? Big difference. And then, is this a way of testing out things you are already doing independently? Launching a creative experiment from scratch? Doubling down on something that’s working? Six months to goof off? It all depends. All can be fine for the right person.

Finally, other questions like:

• Financially, is it risky? If so, how could you derisk it?

• Emotionally, what might it cost you? Is that somehow potentially a way to grow in emotional capacity?

• What relationships will be worse because of it? Can you deal with that in the short term?

• Finally, is it reversible? Can you get back to where you are now?

Ultimately, I can’t tell you when it’s right for you. You need to decide what you are doing and why.

#2 Do you think you are lucky to have “succeeded” in the pathless path? Sometimes I see some comments online about taking a career break / quitting without the next job lined up, people talk about the risk of not being able to find a better job, and say it is not guaranteed everyone would thrive doing it.

You are projecting success onto me.

Others in my situation might feel like they are failing. Others might feel excellent.

Personally, I don’t really relate to the idea of “success” as much as you may not believe that.

One weird thing: I felt FAR better on this path almost immediately, and in the several years in which I was very much just breaking even without much intention to scale, grow, or make money.

Those positive feelings mostly came from the inner game of the pathless path - getting to know myself, my interests, my tradeoffs, my money insecurities, dancing and accepting fear and uncertainty and so on.

I spent the first few years of my path pushing the edges of this new kind of life and seeing what I might actually want to be doing. It was exciting. As soon as I started building my life around a creative practice, I found a life rhythm that felt good and sustainable and then the question was “how do I fund this?” I’ve been able to fund it for 8.5 years and I have some confidence I can keep it going for the next 2-3 years. After that? I’m not sure, but I’ll probably figure something out.

When I quit, I had nothing lined up. It was the first time I did that. It was scary, but it seemed like a better option than jumping from job to job like I did too many times in my twenties. Weirdly, it was not having a plan that enabled me to see how much running away from the present I was doing on my previous path. It forced me to see what I was actually doing, get to know myself, and start to figure out the tradeoffs that really matter.

Also, who cares about this:

“people talk about the risk of not being able to find a better job and say it is not guaranteed everyone would thrive doing it.”

So what. What do you think?

People have this weird tendency to make these broad claims like “well, everyone can’t do Y” to dismiss the possibility. It’s an uninteresting statement. So what? What if I say something like “Everyone can’t hit a tennis ball like Federer,” does that stop you from wanting to play tennis? No, of course not. Some things can be worth doing even if you don’t thrive. I certainly felt like I was fumbling around for the first couple of years there but never thought, damn, I should go back to my former path because I’ll feel less like a fool.

So what I am trying to tell you: I felt successful at the same time I felt like a fool. If there is a feeling I’d attach to success if you forced me, it would be contentment. Until I quit my job, I felt the opposite of that: restlessness.

For some people, they are totally fine with restlessness or just rank career success, steady incomes, money, and fitting in above that inner feeling of contentedness. I don’t, and I know that makes me weird. And poorer. That’s the thing: Every choice has a cost. What are you willing to pay?

We make a lot of tradeoffs that others would not be happy with. I only feel like I’m thriving because I am clear-sighted about the costs and benefits of the path for now and want to keep going.

Is that success? Who knows.

That’s for you to decide :-)

#3 Do you think you will ever go back to a full-time job anytime in the future? Do you think there could be a full-time job in the world that could be even better for you?

I don’t think I’d be open to 48 weeks of 5-day in-office employment. The good news is that there is a lot more dynamism in the labor economy now in terms of how companies are willing to work with people.

I think I could easily see myself in an ongoing part-time role for a company as an advisor, consultant, or something like that. I’ve built up a lot of skills that are probably useful to a lot of companies, but I’ve also learned how to structure different kinds of projects, gigs, and products in ways that don’t require in-person attendance to receive compensation. I don’t think money would make me want to work full-time again as long as I can hack together a modest living on a US salary.

But if our family changed our goals and decided it would be best for me to go pursue income to meet our needs, I would be the best positioned in the family to go earn money, so I’d do it.

But Angie is not pushing me to go to work and enjoys my flexibility as much as I do!

How important is it to have met your wife and have her company in your journey?

Very important.

We never really separated for more than a month after we met. She’s been with me from the early days, and we’ve been co-building this life together. I think my journey would have been a lot harder without her. In many moments of doubt, I felt normal because she was on a similar path.

I talk to a lot of people who say things like “how do you convince your partner to be on board with a different kind of life or path?”

I have no idea. I married a weirdo.

Hey there! I’m still on sabbatical, but I hope you enjoyed this issue

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

How To Leave The “Casino”

There is a lot written on how to build a startup, but not enough written on how to build a solopreneur business. My go-to book for years has been ’s Art of Gig series, but his writing can be a bit challenging for beginners (these books are still in my must read category if you are committed to an indie path for more than a year).

Luckily, ’s new book and workbook, Leaving the Casino, offers an absurdly useful guide on how to think through building a business on your own. What made it great, something I’m excited to recommend, is that it goes beyond tactics and pushes people to think through prompts, frameworks, and a well-thought-out process to go much deeper, focusing on the foundation level of your business.

It’s also pretty funny as she pokes fun of what she calls the “Entrepreneurial Casino”:

The Entrepreneurial Casino is a multibillion-dollar industry built around the dream of entrepreneurship, focused on selling quick and easy solutions to grow your fame and fortune. The influencers selling you these solutions are experts at using every marketing tactic in the book to ensnare you—scarcity, urgency, social proof, even sex appeal. It’s the course-based version of diet pills: fast promises of big results with little effort. This makes the tech platforms the ultimate winners of this game—you pay big bucks to advertise while your attention and data are commoditized and sold to the highest bidder.

…

And when their strategies didn’t work? I was told to try again. Just invest a little more. Take the next course, upgrade to the premium mastermind, “fix my mindset,” and the oasis of success would finally be within reach.

And she goes on:

Because I’ve had such a variety of experiences—engineering, consulting, big corporate businesses, the startup world, and building my own business (first as a life coach and then as a fractional COO)—I can see across all of the different floors of the Casino.

The boss babes and manifestation girlies on Instagram showing off their luxury lifestyles.

The Twitter/X and YouTube bros promising that you can have six-figure revenue months just by writing content for one hour a day.

The B2B marketers turning LinkedIn into a sea of homogenized and flattened expertise that always leads with a “hook.” (Feels like a hook, line, and sinker to me.)

But I can use my experience to curate what does work in business and turn a torrential sea of information and shoddy promises into frameworks and tools specifically designed for small, knowledge-based businesses (like the ones I’ve built myself). The skills I honed in corporate strategy—diagnosing systems, analyzing trade-offs, and building sustainable solutions—are the same tools that can be applied to help entrepreneurs create profitable and sustainable businesses without sacrificing their values or well-being.

I have felt many of the same things and it’s not a coincidence that we both spent time working in strategy consulting before exploring an indie path.

A lot of people like to dunk on consulting but the best part of the experience was being exposed to hundreds of different global businesses and seeing how businesses actually make money. On top of that, we both DID ultimately leave consulting because sometimes it does get caught up in buzzwords, fads, and doesn’t quite deliver.

So I asked Jessica to do a little Q&A for us.

Without further ado, I’m handing it over to her:

The metaphor of the “casino” for the modern state of advice around doing your own thing made me laugh. When did you first come up with this idea?

I left my full-time job in March 2021, and I did contract consulting work while building my own book of business. Later that year, I wanted to grow faster, so I did what “everyone” was doing—I joined a $25,000 mastermind, because in the silo of the online business ecosystem I was in, that was the common step at that point in time.

I could cashflow it from corporate savings (ex-McKinsey, ex-Nike) and my contract work. But I got in the room and looked around—and at least 12 of the other 14 people had no substantial business. I’m thinking: How are they paying for this? And also: Are they even paying full price? Because I was, and I felt like the sucker who pays full freight at a Vegas hotel, while everyone else got their room and drinks comped.

Then we started talking about marketing. At this point, I was building a fractional COO service, and the advice was all about email funnels, social media launches, cohort-style selling. I’m recognizing: This doesn’t fit my business model at all. Nor does it fit theirs, based on their stage of business.

That’s when I asked myself: Who’s really making money here?

Because the person leading the group was making multiple six figures, from people who had no business paying for that level of support.

And I thought, “Of course. The house always wins.”

Once I had that metaphor, everything clicked. What people were being taught wasn’t business building—it was gambling. Spin the wheel on a high-ticket program. Keep pulling the slot machine of social media posting, and hope you go viral.

A few lucky people win big (often due to pre-existing advantages, market timing, or platform arbitrage), and everyone else loses their money.

The hook: “Make six figures from just doing an hour of deep work every day!”

The reality: “Make six figures by getting on Twitter at its peak (and YouTube seven years ago) and build an audience teaching people how to make six figures from an hour of deep work a day!”

I think you do a great job of painting the picture of what a solopreneur path requires. I don’t think there’s been enough written about all the tradeoffs you constantly need to make, and also the variety of tools and content decisions you need to be making in the modern world.

Talking about trade-offs invites nuance. And the entrepreneurial casino is designed to make you stop thinking about trade-offs and just dangle support.

When I tell people it’s going to take two to three years of effort, probably at a minimum, to build back up to their corporate salary, few people want to hear it. One, because that’s not sexy. Two, because many people don’t have that kind of cash saved up to bridge the gap.

So to get the broadest audience, you must sell the dream.

And early on, I believed that if you talk about the trade-offs, no one buys from you.

Gain a lot of followers to have “influence”? You might end up resenting talking about the same topic on a relentless publishing schedule for years.

Build an agency so you can have your team deliver while you’re the CEO? Most agency owners I know make less take home than profitable soloists because of the costs of running their team.

Every path requires the time and effort to walk it, which isn’t an easy sell, especially to newer entrepreneurs who want hope and clear next steps.

I love Paul’s writing because he’s so honest and talks about the tradeoffs. To do entrepreneurship with a high level of creative autonomy and flexibility means his business is less financially lucrative than it could otherwise be.

I wrote this book because I couldn’t find one that articulates the practicalities of how to navigate those trade-offs for expert-led businesses. Many books are memoir mixed with “this is how I did it” to help fuel a speaking career. Mine is meant to be “here’s everything you won’t get from an MBA that I’ve learned from tens of thousands of dollars in programs and years of pattern-matching”.

You seem to find a good balance between engaging in content and sharing online and mostly focusing on your business behind the scenes. I think people who want to work independently feel like they need to be doing social media but that’s not quite true (it’s just the loudest voices telling us that). What forms of content have worked well for you and feel sustainable?

For my business to be successful early on, I didn’t need thousands of followers. I needed five clients.

And replicating what I saw from working at McKinsey, they weren’t posting on social media every day to get clients. They were doing traditional business development—tapping networks, building relationships, building authority through long-form asset creation.

So that’s what I did.

My content strategy is the codification of patterns I’ve seen or topics I want to explore with my clients next.

Every week I write a long-form newsletter.

Every month for three years I taught a free class (not a sales pitch webinar, an actual free business building class). Those classes and long-form content ended up laddering into the book.

And then I guested on other people’s podcasts and guest taught in other communities, because of those relationships I’d built and the frameworks I’d developed.

I’m terrible at anything that requires algorithmic discoverability, like short-form video or tweets/Notes. What I lack in performance, I make up for in relentless consistency.

Now, as I’m moving into more visibility with the book, I need more eyeballs on my work. But in order for me to make money when I started, I didn’t need to have a ton of followers. I needed to have 50 solid relationships.

How long did it take you at the start of your journey to find your footing and have the feeling like “ah, okay, I have confidence that I want to stay on this path”?

I knew immediately I never wanted to go back to corporate. But wanting to stay on the path and having confidence in the path are two different things.

The first two and a half years? I was running from something—toxic corporate environments, doing two jobs with the salary and time of one, poor leadership decisions I could see from a mile away. I hated every moment of the corporate theater shenanigans where I had to spend more time prepping absent leadership for meetings than making decisions.

So I did contract consulting and fractional COO work to pay the bills while building my own book of business on the side.

Around year three, something shifted. I realized the business skills I’d learned at McKinsey and Nike—the ones that made my financial success faster than most soloists—weren’t being taught anywhere. That’s when I moved from running from corporate to running toward something: teaching the foundations that actually work.

It’s taken me five years to feel like I have solid momentum and can take the foot off of the gas a bit related to my pace. Now that the book is in the world, it’s an asset that people can really share that has already started to bring in new people to my world.

You also come from a consulting background, working at McKinsey for several years. For me, experience at McKinsey was invaluable prep for working on my own, but not for the reasons people think. For me, the value was being part of a well-run organization where I could get tons of reps, aiming at a high-quality bar, working at a fast pace, and where everyone around me was always pushing me to do better. I don’t think I could have written a book on my own without this. What stands out from consulting for you?

I couldn’t have written the book without McKinsey. And I couldn’t have run my business without Nike.

McKinsey taught me how to pattern match quickly, how to get to root causes, how to architect my business experiments with an hypothesis-led approach. It taught me to think in frameworks. When you start thinking in slides—when everything has to be bucketized, structured, framed—that shapes how you communicate.

My signature framework—what business are you running—only exists because McKinsey taught me MECE (mutually exclusive, collectively exhaustive). I had to see that this person’s business is fundamentally different from that one, but both are distinct from this third one. Bucketizing and creating coherent structures is pure McKinsey training.

But running my business? That’s Nike.

McKinsey teaches you one pace: on. Full sprint, all the time. Which is why I left after 3 years because the pace was just too intense for me.

Nike taught me rhythms. I worked in planning and inventory management for five years, and you’re thinking in multiple horizons simultaneously. What’s coming from global design three years from now, and how does that information affect what I need to buy based on what I’m liquidating right now?

Nike gave me the rhythms of repeatability. Every season, we ran the same playbook of dates, gates, stages. Every month, similar processes for reviewing results. Those rhythms were ingrained in me through years of leading sales and operations planning processes.

McKinsey taught me how to think. Nike taught me how to operate.

One side effect: my course slides are very dense. At McKinsey, your slides had to be your entire talk track—just put in slide format. My slides still work that way, incredibly dense with all of my thinking on the slides.

You go pretty hard against the promise of passive income, which I think makes sense given how much it’s oversold to people. However, now you have a book in which you will earn income…passively. I’ve come to reframe this as “less than grind” income, or LTG income, meaning its less energy than a job to maintain but still requires maintenance. How do you think about this now that readers of this newsletter are about to purchase your book and send money to your bank account while you sleep :-)

I like your reframe—”less than grind.” I call it leverage.

Now that I’ve done years of learning and years of writing and teaching, it’s much more effective for all of us if I codify that into a single artifact you can consume at your own time and pace, instead of you having to buy my time to share that information.

Readers get a painstakingly crafted book, or buy my membership and get a curated curriculum and set of tools, and know that it’s the best I could make it instead of the best based on how I explain the concept during their call. I want people to spend their time and money on implementation, not just information.

Sure, I’ll have purchases come in while I’m asleep. But what people may not know are the years I’ve spent building a relationship with Paul, supporting and sharing his work, making sure I met him IRL when we were at the same conference, gifting him the book before it came out, etc. Over five years of relationship building which has culminated in Paul trusting me enough to read my book, recommend it, and letting me share this with his readers.

Nothing about that approach is passive. 🙂

Of course, I still make the money I need to fund my life through maintaining an active roster of consulting clients and cohort members—which isn’t passive either.

Who are some underappreciated voices for engaging on these kinds of paths that people may not have heard of?

My favorite two underappreciated voices are Lex Roman and . Lex runs Revenue Rulebreaker, a newsletter and membership collective devoted to publishing the rulebreaking revenue stories of solopreneurs and fostering indie business collaboration. Amelia Hruby runs Softer Sounds, a podcast production studio and Off the Grid, a podcast, book and community dedicated to a vision of the internet where we create, connect & make money online without extractive algorithms.

Okay Paul here again. Please follow Jessica. She is a wise guide in the world of indie entrepreneurship. And purchase her book here.

Check out her book

Reader Survey - Help me share cool data next week?

I shared a link to a reader survey last week. It has some basic demographic questions, interest questions, and a couple of fun questions as well. I’ll share the results of next week in the newsletter.

Start Survey

Also, a few of you said you had trouble logging in to the Substack-hosted survey, so if you want to use a direct link, you can do that here.

#1 Write Once, Read Forever

Today I had a conversation with a reader here in Taipei who had only recently stumbled upon my writing, first discovering the Wise Agency series from last month, and then immediately reading The Pathless Path. It was interesting to talk to someone who had very little context on most of my journey and writing. He was appreciative of the Wise Agency remix of my ideas, even though I’ve been feeling like I’m rehashing the same ideas too much.

It’s a good reminder that my desire to always ship something new, novel, and inspiring is a hard and impossible bar for myself. It’s also why I’m playing with this new format, which is mostly what the newsletter was from 2017 to 2019.

I want to ship interesting essays less frequently and dedicate more time to book-length projects than to medium-length newsletter essays.

We’ll see how it goes!

#2 Some Things I Read & Enjoyed

• ’s book Leaving the Casino is an excellent guide for new indie freelancers who want to build their own solopreneur business but want more substance than the traditional tactic-style advice found online

• I finished The Other Side of Change by . This is a book of stories about people who went through changes in their lives. If you like the kind of reporting style non-fiction books that interweave a bunch of stories about people, you’ll like this book. The writing is down-to-earth, and it doesn’t come with an agenda of any kind. The best part, by far, was the final chapter in which Maya detailed her own challenges trying to build a family, which, given some of our own recent challenges, was relatable and powerful.

• And I also finished Unhinged Habits by . This was GREAT. I loved it so much that I am going to be writing about it next week. I think this will be a great companion for people on a pathless path who can’t quite commit to one thing or one habit forever.

• Vitalik’s essay on popup cities and other experiments in living is very good:

But I also think there is something different at play: people just have to get off their butts and actually create these alternative cultures and environments, and doing it is hard. Startups are also hard. But startups have had a multi-billion-pdollar capitalist optimization machine figuring out all the most optimized ways of doing them and rapidly growing them to scale, and turned them into cookie-cutter standardized playbooks. Culture does not have the same profit motive

• Also, 12 underrated reads from 2025:

#3 Books

just put the finishing touches on her memoir, Made in Taiwan. English translation will be out later this year.

However, if you read traditional Chinese and would like to receive updates, please sign up for her newsletter or express your interest here.

#4 People/Things Worth Following

and new podcast Small Creator, Big World is a great one. Both share the perspective of creating while having full-time jobs in the creator world. I love the frame of a “small creator” and have a video coming out about it, too. They both have great chemistry together, and I’m lucky they are friends too:

Small Creator Big World

A podcast for small creators with big dreams

By Becky Isjwara

#5 A Tweet

I don’t know how the age of AI will change work narratives, but you can already feel it shifting.

Give me more data to analyze by filling out the reader survey before you go

I shared a link to a reader survey last week. It has some basic demographic questions, interest questions, and a couple of fun questions as well. I’ll share the results of next week in the newsletter.

Start Survey (with substack account)

Start Survey (no substack account)

Paul finally wrote a shorter issue, nice

Short for me at least.

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your God-given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

Please fill out the Pathless reader survey:

I’m doing a survey of Pathless readers as I rethink my approach for 2026. Expect more experiments, different formats, and more investment in my community over the next year.

Take The Reader Survey (5 Mins)

Reflecting on 2025

For the eighth time, I accomplished my only real goal: don’t go back to the paycheck world.

The reality is that this year felt like a year of treading water on the business front. I kept feeling a bit stuck, trying to find my way out before concluding at the end of the year that my priorities weren’t really to crush it on the work front anyway. My priorities for the year were:

1. Being a dad

2. Supporting Angie and helping her finish her book, Made in Taiwan

3. My hardcover book launch

4. All the other stuff

I spent too much time worrying about #4 and not giving myself credit for doing quite well on #1-3.

#1 Wrote a bunch of stuff

I spent lots of time tinkering with AI tools, contemplated my relationship with creating and sharing ideas, poked fun at the hustle bros, celebrated my eight pathless anniversary, shared 40 lessons on learning 40, riffed on AI & Work, explored rabbit holes like protocols and seapunk, launched my biggest project, the premium hardcover, and riffed on “wise agency” after giving a talk on the subject.

Looking at these posts from the year, I have a couple of thoughts

• Yes, I was all over the place

• I was a bit more generative and creative than I thought

Behind the scenes, I dabbled and wrote quite a bit in a few book drafts. Those books didn’t really find flow toward a finishing point, but I intend to revisit them in 2026 and see if we can ship 1-2 of them and/or experiment with new ways of producing and publishing books and mini-books.

As always, the goal remains: “write most days.”

#2 Did some podcasts

I published 13 podcast episodes, and 3 of these were me being interviewed on other podcasts. It’s clear, I can’t quite sustain the podcast right now, and I’ll still post episodes here and there, but don’t expect to spend much time on it in 2025.

Some of my favorite episodes this year include the convo with Nat Eliason on writing books, Steven Foster on his pathless path and living in Idaho, Andrew Taggart on The Yoga of Work, Pranab Sachi on “attentional co-piloting”, and Dennis Owen on The Art of Retirement.

#3 Business Kept Operating

Behind the scenes, my businesses kept humming. Most income flows are down year-over-year, but still enough to fund my life. People kept buying The Pathless Path, and my consulting skills course seems to still have a market despite declining over the past couple of years. I also did a few corporate workshops, which helped my confidence throughout the year. I plan to share more, but here is a high-level picture of the year:

Most of my income and profit came in the fourth quarter from sales of the hardcover and black friday sales from my consulting course. This was the first year I was in a bit of a panic financially in terms of needing new sources of revenue, but it feels good to finish the year solidly in the black, earning about $10-15k more than our cost of living.

My margins were about 43% this year, but if I subtract out the hardcover investment, they were closer to 70%.

I’m looking forward to getting back to running a leaner and more profitable operation next year.

Here are some reflections earlier this year on my eighth! year in business:

#4 The Hardcover Feels Like A W

I’ve never made a big bet like this before, but for me it feels like a W already.

My modest mental goal was 100 books, and I ended up selling about 325 via 250 of the launch and premium buy-one-gift-one bundles. This generated about $35-40k in revenue, which paid off about half of the investment. I had a huge bill of $36k in November for the remainder of the printing costs for the notebooks and books, and it was nice to be able to pay for it with sales rather than have to dip into personal savings.

I was able to fully fund the investment from cash flows from the business, and my mental accounting is seeing this as a past sunk cost, meaning 2026, all sales will be cash flow positive.

This tested me mentally. I’ve never frontloaded money into a project at this scale, and it definitely stirred up some anxiety. I wrote a bit here, and if you didn’t read my essay on the “why,” you can check that out as well

#5 Expanding My Store

The direct sales experience has gone really well, and I’ve decided to expand the selections in my Shopify store. You can now purchase paperbacks, ebooks, notebooks, the pathless hat, and bulk copies of the premium hardcover directly from me.

My hunch is that direct sales will be a big part of making this author path work by producing one-off collectible items, offering bundles, and also signed books.

The premium hardcover bundles will continue to be available with gift wrapping, free notebooks, and illustration cards until I decide otherwise, but you can now buy the notebooks (which people really love and are nicer than you’d expect) on their own now:

Shop The Store

Still figuring out Shopify and such, so if you have any feedback, do let me know!

#6 The Community Is The Most Energizing It’s Been In Three Years

I launched a community in 2023, and the first year never quite worked with the monthly payment model (too much churn and admin work to handle it). Since shifting to a one-time fee, it has grown, attracted a vibrant group of people who are active in sharing and connecting with others, and it resulted in us shipping our first print project (via The Pathless Collective), not to mention many offline connections.

One big improvement was shifting away from Circle and to a WhatsApp community, which is about 10x more active and a medium I am better at engaging with.

It doesn’t make much money right now (about $4-5k in 2025) but it is something I find myself pulled to more these days. If you’d like to join us, one of the members is going to be hosting a deep reading group starting in January (will share more when I have it), and also hosts weekly serendipity sessions.

#7 Had so much fun being a dad

I’ve been thinking about the idea of “quantity not quality” when it comes to being a parent to a young child. This is mostly because when you’re with a young child, especially a 2-year old, the time is not “high quality,” its usually pure chaos. Yet the more time I spend with me daughter and the more time we spend together as a family when we are not rushed or stressed, the happier I am.

I feel so lucky to have a delightfully happy, silly, and fun daughter. I’ve had so much fun spending ton of time with her over the last 2+ years and its by far been the highlight of the past few years. I've become sillier, more playful, and happier despite many challenges on the health and work front.

Sometimes I feel like my path is a bit crazy and that eventually, its not going to work anymore. That may be true but I think I’ve been to stressed about it. My “compensation” for this way of approaching life has been tons of quantity time with my daughter. And I wouldn’t sell it for anything.

#8 Taking Some Time off At The Beginning of 2026

I’ve taken half-action on too many small things over the last couple of years and am not finding forward momentum on enough things. Instead of trying harder, I’m going to take my own advice: “Have you tried doing less on the problem?”

We’re starting the year participating in a “Traveling village” with 20 other families in 3 different countries from January to May. I decided I’ll take a break from January 7th until the end of the first location, February 21st, and likely until the end of February.

I used to take “leisure weeks” every seventh week, and they really helped me both connect with what I’m deeply driven by AND take action/ship stuff. That’s fallen off since I finished Good Work in 2024, and I’m going to see how this mini-sabbatical goes.

Please fill out the Pathless reader survey:

I’m surveying Pathless readers as I rethink my approach for 2026. Expect more experiments, different formats, and more investment in my community over the next year.

Take The Reader Survey (5 Mins)

Finally, thank you!

You have no idea how grateful I am to people who engage with my work. The fact that this path is still going and I get to work on interesting things and spend my time in a way that feels good most days is remarkable.

If you aren’t getting what you want from my writing or work, though, please unsubscribe.

There is so much good stuff out there!

Order the Hardcover

This is part of the Wise Agency series. Click here for all three parts.

In the last post, I covered the period of “getting lost” and arriving home to “wise agency.” It’s a remix of past ideas I’ve written about, but in the context of an interesting 2x2 framework, with some fun visuals I created using Google’s latest image model. You can read the first two installments:

This post is a continuation of the “wise agency” part of the quadrant, which, for me, is just the beginning of acting in the world from a new perspective, a journey that basically will never end. In the last eight and a half years of this journey for me, I have not really moved past a feeling of “beginning again.” I suspect this never ends, in a good way.

More specifically, I wanted to focus on a few things that almost everyone struggles with and some useful ideas and frameworks that might help with:

1. What to work on

2. How to do it

3. When and how much to do it

Zooming out, these are pieces of a book that was never finished, something I was tentatively calling a “creator’s field guide,” something I’ve now chopped up into Good Work (published!) and Buy Your Freedom (publish date: TBD), and delivered in several workshops over the last year.

There’s a lot of interesting stuff in that draft that I want to share in some form, so I’ll likely be sprinkling it out via the Substack in 2026 or thinking of fun ways to launch it as a lower-lift book in digital form (if you have thoughts, let me know!)

First, how do you know what to work on?

One of the biggest fears people have about making a life transition: I don’t know what I’d do with my time.

Most people who do end up making a big change in their life either don’t have this fear or have said, screw it, I’m going to step into the unknown anyway.

They typically have one or two things going for them, too:

1. They’ve either been dabbling with projects, identities, or interests that don’t fit their current life, and they want to do more of them, or

2. They have reframed needing to be perfect at everything to seeing life as a series of experiments, most of which are allowed to fail

   1. Shoutout to who wins coined phrase of the year with “Tiny Experiments,” the title of her book, which lays out this shift

My spin on doing tiny experiments has been something I’ve called “Ship, Quit, and Learn.”

Since 2018, I’ve taken this approach with launching experiments, focused on three things:

1. What can I ship quickly?

2. What’s the off-ramp? How do I design it for quitting?

3. What does the experiment tell me about what to do next? (What did I learn)

This is the opposite of what many people think they should be doing.

Most of us grew up in a culture and schools that teach us a lesson we must unlearn: That we should always do our best to get an A on everything we do.

This is a bad approach if you are embarking on a new path because the goal is not to be universally successful, but to keep learning and evolving without re-creating the path you are moving away from.

The way to do this is to try lots of stuff.

Without this shift in aims, many people will re-create the same problems they just escaped because they are using the same strengths and tendencies as they did before.

The point of wisely acting in the world is to step into new terrain and to create new possibilities for living your life that you couldn’t quite access before. This requires embracing new emotions and new behaviors despite knowing there might be more productive and expedient ways forward

The thing I like about being self-employed is that I can try tons of stuff, somewhat without anyone noticing. When employed, a new experiment looks like a dramatic job change. Now, I can spin something up or shut it down quietly within a couple of days.

Here are dozens of the legible experiments I’ve tried over the past ten years, most of which have “failed”:

Beyond this, there are probably 100 other things I’ve thought about doing that I haven’t taken much action on. Usually, it’s because I’ve tested the thought with people and saw a lack of resonance, or I decide to wait a bit to see if I’m still excited about it. My recent hardcover book is an example of a project that I couldn’t stop thinking about.

Over the years, I’ve stolen a bunch of decision-making heuristics from others to help me make decisions and get better at starting and stopping various endeavors.

These six decision lenses help me look at things from different perspectives and override some of the more base impulses that drive us to chase various things:

1. If you knew it would fail, how would you approach it?

2. How excited are you on a scale of 1-10? You can’t pick 7. Only 8+ is a yes

3. Hell yeah or no. Simple.

4. How much would you pay for the opportunity to work on the project?

5. Is it a “full body yes”?

6. Am I deciding to be myself and follow what I want, or am I deciding to try to manage the future or a future projection of myself?

As an example, using question #4, I realized I’d pay $1,000 to avoid a project two years ago. This gave me the confidence to make a strong counteroffer on my terms, which turned the project into something I was excited to do and paid me twice as much money.

But many things, especially if they are new, novel, or weird, still require a leap of faith. No decision framework will ever give you perfect information. The goal on a path of wise agency is to be pushing the frontier of what you are currently capable of and what is slightly beyond that, all aligned with a growing intuitive sense of what is “right” for you.

has a great phrase here, “do the weirdest thing that feels right.” That’s what I’m talking about here.

This doesn’t stop people from wanting a playbook. Many people approach me now and ask how they can sell a lot of books. While I’ve written 7k words on my marketing efforts, I still would claim that I don’t fully know why anything worked.

All I could honestly say is do exactly what I did: Spend years on the wrong path, but developing tons of skills that will later help you be a good writer. Then quit. Decide to write more consistently after a year. Then, write without attempting to make money from writing for years without any goals. Talk to literally anyone who wants to talk to you about work, optimize your project selection and experiments around interest level and fun, and all along the way, live well below your means so you can keep buying time to keep going.

Oh.

Most people just want a magic book launch playbook.

The reality behind most people’s successes, if they are honestly willing to share it with you, will look messy like this:

This only “worked” for me because, along the way, I was enjoying what I was doing, getting better at selecting projects, and becoming wiser about a meta-game I was participating in.

As I was in the midst of all of these projects, I kept trying to make sense of my own game, learning about what was working, and trying to be honest with myself throughout. This tendency to sensemake my own path has resulted in many fun diagrams over the years.

From 2020:

2021:

2022:

None of these are perfect representations of my path. But all capture my attempts to play a long-term game without legible money or status goals as the priority.

I think one thing they do capture is the confusing state of going against the default games that most people are playing. I suspect that if you are also rejecting default aims, you must develop your own frameworks, sets of principles, and a good understanding of the trade-offs you are making.

Each time I write about what I’m doing or create a new framework, I am reality-checking my own internal storytelling and then exposing it to public criticism.

This has helped me remain honest with myself. If I were claiming success but were not financially viable or satisfied with the way things are going, what the hell am I doing?

Some people can’t tell a story that doesn’t align with how they show up. That inconsistency drives me nuts, so I use it to my advantage.

Second, how do we think about our relationship to the work?

Too many people try to fit themselves into existing paradigms on new paths.

They look at what other people are doing and think: I will do that!

Everyone is doing a Substack subscription, so I will do that!

Everyone is making money on Substack doing X. I must do that too!

This is a fine place to start if you are still learning about what works, but eventually, you need to move on to what works for you, for long periods of time, independent of outside forces.

This is really hard, but it is something you should almost always be thinking about. If you are someone who is going to take a shot at being an independent consultant, you should definitely have models of pricing, offerings, ways of working, and different styles. In fact, learning about the range of models is vital early on. But eventually, the point of the work needs to shift away from copying what works to you making choices that will help you naturally evolve into a style and way of working that only you can inhabit. You can probably map this to any sort of life mode beyond work, for example, parenting.

The reason copying other people is not wise is that you are not in a position to be adaptive. You are at the whims of a complex system that is on the edge of chaos and will keep changing.

A shift I encourage people to make is to Don’t Find a Niche, Find a Mode. As I wrote:

Find a mode where you can continue to be excited about what you are doing.

Find a mode where the friction to getting started declines over time.

Find a mode where you are excited to keep going despite being ignored.

Find a mode where you want to do something despite not having anything to show for it or in the worst case, despite criticism.

After I quit my job, my niche goggles made it very obvious that I could morph myself into a character in the LinkedIn corporate thought leader space. There are lots of legible opportunities, speaking gigs, consulting projects, and status up for grabs, plus lots of models to copy like Adam Grant and Simon Sinek. I quickly realized I was not wired for it. Clear ways to make money, sure, but I couldn’t see myself giving a talk to Accenture, telling people how to adapt to The Future of Work™.

Instead, I accidentally focused on finding a mode: finding projects and kinds of work that I actually enjoyed.

Within a couple of years of doing things on my own terms, most of which didn’t have any clear path to financial payoffs: oh, I can keep doing these things for a long time!

I realized this was quite a strong tailwind I could ride for years.

The advantage of finding a mode, and sometimes “wasting” years trying to inhabit and embody this mode, is that you can later insert yourself into a niche world and know why you are doing something and on what terms.

If someone wants to hire me to give a $25k opening speech for Simon Sinek at the Accenture ITCorps AI APAC offsite, I’d be happy to do it, knowing I could playfully embrace the role of LinkedIn thought leader guy, have fun with it, and not be subject to the constraints of being that person for the next ten years.

People who embrace finding a mode early in their lives or a reinvention journey are also confusing to observe. They flow from project to project or interest to interest with much more ease than people expect. They write a book, then launch an app, then do a course, and then take a mini-sabbatical. is a good example of embracing this. Every time I hear from him, he’s launching something new, but it sort of makes sense. He’s built a life around literally just being himself.

The hidden trap of “find a niche” is not that it doesn’t work.

It’s that it will work, and you will waste years of your life on the wrong path, doing things you don’t actually want to be doing.

Finding a niche is an intellectual stance toward life. It is about figuring out what you need to achieve certain outcomes.

You need to know what niches are, how they form, and how they lead to very different financial realities. For example, if you love writing about finance, you will make a lot more money than if you love writing about buttons, or even work.

Finding a mode says, “okay I see how the world works. I see the niches. I am aware of them. I might make some changes in terms of how I communicate my thing to adapt to that a little. But at the end of the day, I’m going to keep making choices such that I have more opportunities to keep making decisions as a person that I don’t need to pretend to be.”

Third, how much and when do we actually work?

Most of us know that work days are Monday through Friday, and when many people become self-employed, they go through a phase of still showing up Monday through Friday and performing a normal workweek.

I urge people, however, to remember to fire the “manager in their head” and take the next Tuesday off. Most people would benefit from a lot more experimentation and asking some questions that help you zoom out:

• What is the ideal work month?

• What is the ideal work year?

• What are the months or years of work that I now have trouble remembering?

• What would my year look like if I had to work in four seasons?

• What are the work projects that seem more satisfying to reflect on, the more time passes?

• What is your ideal work decade?

A good way to think about spending your time is this 2x2 of life quality and mindset:

This gives us four ways we can approach a project:

• Grinding: Working as hard as possible on everything

• Small bets: Doing a bunch of small experiments while eliminating risk

• Sprints: Intensive building for weeks or months that are followed by periods of rest

• Long-game: Work you are designing your life around that you know you won’t quit because it’s so important. You find the right pace that works for your life

Over time, as people get smarter about what they want to work on, they focus more and more on their “good work” over a long game and more strategic bets that they can sink a bunch of time into over periods of weeks or months. But they also probably do different kinds of work in each of these quadrants.

Over time, many people shift to shifting between consistent effort on things they enjoy doing and short-term sprints that might be the key to getting things done or shifting momentum. For my recent hardcover launch, I’m in “sprint mode” sharing the book and promoting it. In this mode, I have a lot more energy for a lot of things like writing this Substack and tweeting. But it’s not quite sustainable as I’m not building in enough time for exploratory work, time in leisure, and at the gym. At the beginning of the year, I’ll anchor back into long-game mode around slow “most days” writing.

The key with this right-hand side is that it is moving in the direction of doing things that you actually want to do. You aren’t pivoting to a crypto ICO because it will make a bunch of money, but force you to repair reputational damage. You are making bets on your future self and interest and on where you hope you might evolve to in the kinds of work you want to keep doing. As always, this is hard to aim at, but the thing that does become more obvious over time is what not to work on.

The sprints are a way of ramping up the intensity of things you are already doing, but in some new way. It’s a way of testing new hypotheses, new kinds of work or products, or new ways of showing up in the world. It could be something like “I’m going to experiment with consistently posting on Instagram,” to “I’m going to host an event at my house in two weeks,” to “I’m going to go home early every day and hang out with my kids.”

I’m doing a “sprint” around my hardcover launch to test the viability of selling books directly right now. I’m chatting with people buying the book, doing podcasts, writing about the experiment, and reflecting on my feelings about the project. It seems promising, and it’s changing a lot about how I think about the next couple of years of how I share and sell my work. But I’m also going to slow down a bit and approach it more deliberately in the new year.

The sprint compresses time, a variable you should always be playing with. Sometimes it’s best to do nothing and go slow, waiting to see what might emerge as if you are a big game hunter. Other times, it’s worth going a little faster, executing on clear opportunities or pathways to different futures.

How to balance all of this

The best framework I’ve seen for bringing this all together is ’s “choose 2” triangle framework in his must-read indie classic Art of Gig.

On an indie path, he says that you must pick two of three and face the consequences of your decision:

1. Autonomy of Goals

2. Integrity of Methods

3. Standard of Living

I like the triangle framework because it forces hard trade-offs. If you choose to optimize for how you work and what you do, you’re likely going to face financial challenges.

This is mostly the side of the triangle I like hanging out in.

But not always!

The hack, as he says, is to make different tradeoffs for different situations:

if you want to stay in the gig economy, you can hack the triangle! Yes, you have to pick two of three, but you don’t have to make the same choices in all situations and at all times. You can rotate through them in various creative ways! This creates a much more unstable lifestyle, but it allows you to address the root causes of the pathologies that lie in wait down each pure path. It’s like keeping a set of spinning plates spinning by darting among them.

The three ways he suggests to do this are:

• Have multiple parallel gigs with different trade-offs in each: I have a lot of things I’m usually working on at once and am usually making slightly different trade-offs in all of them.

• Make different choices in different seasons: This is mostly what I do, shifting focus to my consulting training workshops whenever I need money and then going into unhinged artist mode after

• Made different trade-offs in different elements of the projects: For example, you might be willing to make compromises on how your book is packaged or sold, but not on how it is written or structured. For this substack, I take the writing much less seriously than I do my book projects, as another example.

I think this is a good summary matrix as it gets to the point that is behind almost all action in the world: it’s all tradeoffs all the way down.

The most interesting work, however, is often on the other side of rejecting the standard trade-offs that most people see as reasonable and finding the ones that may be unreasonable for others but are fun for you to make and keep making.

Ultimately, I don’t know much about “wise agency.” I’m still not quite sure what it is. But I have learned quite a bit about what I want to do, what I don’t want to do, and expect to continue learning quite a bit about it for years.

I hope I can look back on this little series in a few years and laugh because I have become quite a bit wiser.

Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your god given right, and there is plenty of other good stuff online.

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If you missed it, I put out Part 1 of this Wise Agency series yesterday. Catch up here:

This is part of the Wise Agency series. Click here for all three parts.

On Wise Agency, Part 2

Ok, in the last post we left off in the lower right quadrant of this remix of ’s idea of the agency 2x2:

You’ve grappled with your “reality tunnels,” decided to step off the default path, avoided the ditch of negative imitation, and are ready to get lost.

Onward.

Phase 3: Surrender & Get Lost

A strong belief I have from talking to several hundred people over the last decade about work: I believe the continuously-employed adult life is unnatural.

I suspect that the vast majority of people would benefit from occasional short- and long-term breaks from their work lives, and more importantly, their work identities.

This is not to say people should follow my path and go full pathless, become self-employed or an entrepreneur permanently. But I do think most people working today would benefit from elevating the importance of looking for time and space in their lives to get lost, embarking on season of solitude, wandering, or adventure.

But even if you pull off such a feat, it’s still hard to surrender fully to such a phase.

After quitting my job, I reflexively rejected many of the the replacement identities on offer: venture-backed founder, tech worker, impressive freelancer, “thought leader.” This is the trap of phase two I talked about yesterday.

In my mode of rejection, I still had the feeling like I should be doing something.

This tension nagged at me for nearly a year as I floundered around the US for about 15 months taking freelance gigs, booking random trips, and flaneuring around Boston.

Then, I booked a one way flight to Taiwan. Perhaps it was a seed inside of me from my future nudging me in this direction or just my acknowledgement that wandering around the US begging my full-time employed friends to hang out with me during the day. It doesn’t really matter. But arriving in Taiwan was enough of an environment shift that I finally gave myself permission to not have a plan.

It was time to wander in the metaphorical wilderness of my new path.

I shifted from trying to do things to trying to do nothing at all.

Which was confusing.

I had this inner exuberance about shifting in this new direction but also felt immensely stuck. I’ve never accomplished or done so little.

I was in what in his recent book, Conscious Accomplishment, calls this “inner purgatory”:

Inner purgatory is the intermediate state between focusing on your inner work and feeling invigorated to take creative action in the world. When you’re in inner purgatory, you desire to accomplish things from an updated perspective, but find it inexplicably difficult. You may struggle with a lack of motivation, inspiration, or energy for external goals, despite knowing that you want more for your life than doing inner work all the time.

Activities that once came easily may feel difficult. You may no longer feel like you have the same raw horsepower you once did. You can try to will yourself to push through things, but without the natural force behind you, you eventually exhaust yourself.

Underneath it all, I was rewiring myself. I was letting go of my past anxiety-driven achievement patterns and toward ones that were more natural and driven by self-awareness. But this didn’t just happen. It was a process.

I needed to let go and mourn the loss of my inner grinder, as I wrote about in Good Work:

Letting go of a life strategy that seems to be working can be terrifying. For me, it meant stepping away from a formula for life that provided me with money, status, and real confidence. I loved feeling competent and being good at what I did. So realizing that I never wanted to return to that world initially filled me with grief. I do miss telling people about my impressive achievements and watching their eyes light up with instant respect.

This period was tough.

I was scared to tell people close to me what I was doing, or really what I wasn’t doing. I lied. I made up fake plans. But I could see that the instant respect I used to command was gone. I still craved respect and hadn’t fully sat with the insecurity of not having that anymore. Comments from other hurt.

What is your plan?!

There is none. I felt lost. Intensely lost.

But like I said, underneath, I also had this deep sense of okayness. I knew I was on the right metaphorical path even if I couldn’t “prove” it. I’ve quoted Rebecca Solnit on this so many times because when I read this line in her book The Field Guide to Getting Lost during this period, it send a jolt through my body:

That thing the nature of which is totally unknown to you is usually what you need to find, and finding it is a matter of getting lost

Getting lost is beautiful.

But this phase can be a trap too!

If you spend too much time being lost, distancing yourself from the default world, things can quickly turn into escapism.

Just like its easy to quickly embrace a new path after quitting your job, its just as easy to immerse yourself into groups where being lost is a permanent lifestyle.

• Spiritual paths to enlightenment

• Productivity & personal growth toward endless achievement

• Seasons of “healing” and therapy and inner work that never end

• Psychedelic and reality altering substances or communal practices

• Going to Bali and not being able to live “back” where you left behind

The key with these things is to embrace them to leave them.

• Go to Bali to eventually be able to leave metaphorical Bali (I did this for two months in 2019, it was a perfect place to hang out 1.5 years into my journey). You can even stay in Bali but you don’t want to live in the reality of Bali

• Embrace the productivity hacks to leave the productivity hacks

• Do the psychedelics and healing work to be able to leave the healing work behind

You’ll also be tempted to join the mob against the world you left behind.

The way out of this phase is to realize that no escape is possible.

You have the desire to be saved but you should stop trying to be saved. You must finally accept that you need to navigate uncertainty, doubt, and vulnerability and befriend them instead of running from them.

For me, Joe Hudson’s work has helped me understand the rough process I took to get out of this: befriending them.

Before this, I spent 10+ years in what Joe calls the golden algorithm: Run from emotions only to re-create them from my action. My formula was simple: Try to escape my current situation => run from emotions => search for another job => praise and validation => feel same dissatisfaction again => repeat.

The way out was simple but hard: feel the emotions. Fully.

Getting lost and making your way out is about accepting it all:

• The uncomfortable emotions

• How you may not be a fit for the default world anymore

• Your frustration at how things work

• The many new challenges you are facing

• How others aren’t open to your new perspectives.

And saying, ahhhh yes, this is okay, let’s keep going.

In other words, you can leave the world but you must leave the world in order to find it again. You can leave work temporarily, only to find it again in new form.

Phase 4: Wise Agency

It’s exciting to think you can arrive at the magical upper right quadrant, the place Peter called “agentic sage,” in his first post.

I think the only realistic way to arrive there is to completely lose interest in any such arrival.

The key idea that I picked up in my season of solitude was that only through knowing thyself can one figure out what is worth doing.

This inverts the logic that we do what others around us are doing or that we should do what is “smart” or best practice. But when you approach life in this way, you can end up making interesting choices, ones only you can make. This looks like “agency” to others but weirdly will not feel like you are doing much at all.

One frame that’s helped me think about knowing thyself is John Vervake’s “four ways of knowing” or the 4Ps:

• Propositional (facts, concepts)

• Perspectival (other peoples ideas, other viewpoints)

• Procedural (how to do things, process)

• Participatory (active engagement with)

Early in our lives, most of us over-index in the propositional (“I know these facts”) or the procedural (“this is the correct way to do things!”).

A movement toward wise agency requires embracing all four and then continuing to engage in these throughout life, ideally moving away from the propositional and procedural as you learn more about yourself and the world.

As you enter a new phase, you inevitably engage in new modes. For me, some of the ways I engaged were:

• Perspectival: Travel to understand new ways of living and opportunities; podcasts to understand new perspectives

• Procedural: Books to understanding how to approach new problems; courses to understand how things really work

• Propositional: Learn basics like tax law, accounting rules, and realities of making money on my own so you can ensure you stay in the game

These give you confidence about your new path and enable you to see new possibilities for your life that you didn’ see before.

But the trap is that you lean too hard on the ones you are best at: The engineer who leaves their job spending all their time on reading how-to books and prodctivity hacks and only spending time trying to make money in the new startup, who forgets to take a day off to assess what might have changed after shifting in this new direction.

This is why the last one and most overlooked is Participatory knowing: through action I can come to know more about myself and the world.

This can be a broad definition of participation:

• Offering something: supporting family members, mentoring people, giving encouragement, sharing your expertise, being the person who reaches out

• Hosting and gathering: dinner parties, book clubs, online communities, group chats with intention, workshops, retreats, or even just a group chat

• Doing new things: taking a class, volunteering, joining a sports league, learning an instrument, showing up to local government meetings, traveling somewhere that challenges you

• Creating something: a business, a piece of writing, a podcast, art, a newsletter, open-source software, a course, even a journal entry

• Religious or spiritual practices: Religious groups, Meditation, mindfulness, breathwork, retreats, and the endless list of woo- and woo-adjacent practices

This kind of participation in the world is increasingly important the further you are away from any sort of default path you left behind.

Vervaeke argues that the modern human needs an “ecology of practices” to stay sane. For me writing has been a powerful practice but so have things like meditation, breaks from work, time with my daughter, breathwork, travel, and all of the weird work things I do in public that stir up all sorts of emotions and discomfort.

On a podcast, he said the aim of these participatory practices if to be open to failure:

An ecology of practice is a complex dynamical system. It takes a time and effort and commitment and a willingness to transform and fail and learn from mistakes in order to make this work.

This rhymes with Peter’s frame of being “less foolish” rather than seeing “wise agency” as a place for arrival.

A metaphor I offer for this is Posting:

Posting is not just about posting online but it can be that too. It is about making an offering to the world. It is moving in the direction of things that feel scary but feel right. It can be any form of participatory action. It is ultimately about making an “opening offer” to the world and being okay that nothing may come back while also being open to whatever may come to you regardless.

At it’s core, “posting” is a generous act, and it is a multi-player game.

I think this is an important metaphor because so many people have reflexively rejected the digital age. Cal Newport tells us to run from the internet, hide in your cavern and do your deep work. I think in today’s age this is the wrong stance.

Real growth comes from engagement. Dancing in the chaos of the world as it is and being open to seeing where you might be able to take wise action.

The biggest challenge for most people is that wise action is very hard.

This is because many of the things you learned about how to operate in that first chapter of your life will no longer be effective.

Either because you are not operating with the same source of fuel (things like the desire to prove others wrong), or that the rules of the world you are now inhabiting and participating in are different.

But now, you have some sense of what you are capable of and more importantly, not capable of. Having this wisdom enables you to hold everything you do much more lightly. Success isn’t your savior and you don’t attach yourself to script of being special through work. This opens you up to the ability to be immensely existed by what others around you are doing. You are amazed at how little you are threatened or triggered by their accomplishments. You don’t feel as much pressure from your projection of “the world” about what you should be doing.

Despite this, you will be constantly tempted to take shortcuts. You will be shown quick paths to riches, easy ways to sell out what matters, and hacks that will enable you to do things the easy way. You will be offered instant acceptance in new groups that promise belonging and a refuge from the world. This never ends.

But wise action is knowing that all of these things are paths to foolishness.

Wise agency is about knowing that the path forward in the world is usually just about surrendering to the work and ways of life that become more obvious over time, through simply continuing to show up in the world.

It may seem like you are arriving when you realize all of this. That you are smart.

But you are wise enough to know that you are still on the beautiful journey of life.

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I recently launched my premium hardcover version of The Pathless Path. If you order before Christmas, I’m shipping it out gift wrapped (custom note optional) with a bonus notebook and note cards.

check it out

This is part of the Wise Agency series. Click here for all three parts.

I gave a talk for ’s Stoa last week around the idea of “wise agency.” It was a fun topic to think through.

Agency is an idea I’m partial to, and I wrote about it in The Pathless Path in the context of Fromm’s idea of “positive freedom.” Positive freedom, in my interpretation, is about leaning fully into your own genuine path and the things that you actually want to be doing, in a sustainable, life-giving way. Agency was the mode of practicing such freedom through experimentation, spontaneity, and discernment about what a good life looks like for you.

In the past couple of years, however, “agency” has become a meme in itself. It’s a suitcase word that can describe anything from ironically ordering 153 chicken nuggets at 2 am to celebrating one’s preferred authoritarian leaders crushing their opponents.

At its best, it is used to describe people moving on a positive trajectory in their lives. We can call this “wise agency.” And at its worst, it’s a cynical or nihilistic embrace of do whatever you must do to achieve your desired ends, regardless of the fallout. Or simply, foolish agency.

Sadly, I see this cynical stance everywhere. From the widespread embrace of gambling and speculative trading to the loss of interest in committing to work without immediate payoffs (or asymmetric equity payoffs) to the embrace of sketchy tactics to make money online, we appear to be going through a period where we have more agency than ever but seem not to have any idea what to do with it.

This has all made me a bit tentative to write much about agency. After all, how foolish must I be to think I have any of this figured out?

After my initial rejection of his offer, Peter pushed me to do it, and I’m glad I did. I’m not sure I have anything novel to offer here, but I do have a better understanding of what I’m trying to do in my own life.

This post got a bit out of hand, so I’m sharing part 1 here. Part 2 will follow…sometimes in the future.

The Problem With “High Agency”

For this talk, I’m building upon Peter’s ideas in a great piece titled, How To Win Friends and Get Things Done…With Wisdom. In it, he argued a similar notion, that “Highly intelligent people with high agency can win many ‘friends’ and get a lot of things done, but they might be doing so foolishly.”

He came up with the following 2x2, which immediately became its own meme, as added a simple red line, showing his journey.

As Peter responded:

Exactly!

It maps to my personal journey.

• NPC. You don’t take the “blue pill”; you’re born into it.

• Agentic fool. Unexamined success = unquestioned “good.” Hustle, hustle, hustle until burnout.

• Spiritual bypasser. A spiritual emergency happens. Aliveness. A new way of being opens up. You overindex on it. It becomes impotent.

I’ve experienced a number of these phases too.

I’ll attempt to map my experience and add my spin to it.

Phase 1: World-Class Hoop Jumping

This was me at 32:

• Working for CEOs & Boards of the biggest companies in the world

• Knew how to “hack” the career game, networking my way to new jobs, and how to break into top-tier institutions

• Guaranteed career path for even more $$, success & status

• Living in New York City

I knew how to play the career game. I felt agentic, or at least if I heard the phrase “you can just do things,” I would have thought I was doing it. Friends would come to me and ask for help, and I felt like I had some secret knowledge of how the world worked because when they followed what I said, it often worked.

But I was a fool.

• I didn’t stay in a job for more than 17 months for eight years

• Constantly wanted to escape my present to an imagined future

I couldn’t see the frame, and even though I’d poke at the edges, I kept moving forward playing the same game.

I was stuck in a cycle of insecure agency.

My “moves” from my early twenties that did improve my situation were no longer useful. They were keeping me in this vicious cycle: I needed to keep moving to avoid what was really bubbling under the surface.

The thing that tipped the scales for me was a growing disconnect between my intense desire to learn and explore my curiosity and the scoreboard (my income).

Eventually, I got to the point where the costs of this diminishing intellectual curiosity were no longer worth it.

But how do you start to see these unconscious scripts you are following?

I personally love Robert Anton Wilson’s frame of “reality tunnels.” These help us make sense of “the muddle of existential reality or ordinary experience,” and the more we are hypnotized by them, the more our “existential experience we then edit out or blot out or blur into conformity.”

One thing I’ve realized is that many people will say things like “oh, society is forcing us all to do X.” But after asking hundreds of people the scripts and stories they grew up with, I found something much more interesting.

1. Most people may have more beliefs and unconscious scripts than they think

2. Our strongest reactions to others’ scripts and our own indicate our most interesting avenues of exploration

In workshops, I’ve been asking people to go through 15 sets of statements and to give themselves a +1 if they have an extremely strong negative or positive reaction.

You can do it too. Go through these and +1 if you react strongly

• “I must consistently improve to be a good person”

• “Anything worthwhile requires suffering”

• “Work hard, and you’ll be rewarded”

• “You should always do the hardest thing possible in your life.”

• “Get good grades, get to a good university, and you can then do anything you want.”

• “You don’t have to enjoy your work. Work is just to pay the bills.”

• ”You should love what you do. Work is the most important thing in the world.”

• “Anyone not doing inner work is sleepwalking through life.”

• “Playing society’s default game is a sucker’s move.”

• “The contemplative life is the best life.”

• “Rich people are worse people”

• “Money is just a flow of energy”

• “Don’t be a sucker, everyone is trying to get rich”

• “My spiritual journey is the most important journey”

• “A pathless path is fundamentally lazy”

Feel free to put your score or reactions in the comments.

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But the key reflection here is that, “wow, I have more going on than I thought.”

Many people often follow this thread and eventually decide:

It’s time to blow it up.

Phase 2: Blow it up

Blowing up your life is underrated. Reading Life is In The Transitions made me realize that our lives are already being blown up all the time, so better to lean into it.

Like Peter’s initial diagram, this is often a period for easily falling into the traps of becoming an agentic fool. You’ve thrown off the shackles of your own reality tunnel and are now SMART. You know the game you were playing and exited.

But as soon as you start walking in a new direction, you see traps around you.

The fundamental challenge is leaving behind your previous path without identifying with the rejection.

In other words, reject the default path, but don’t turn rejecting the default path into your personality.

But this is incredibly hard!

In today’s world, there are an endless number of people who understand that they can turn the vulnerability of not knowing what’s next into profit.

We are often tempted by two forces:

Comfort in conformity, as Jed McKenna warns: “The first thing we want to do when we begin our journey is find the companionship and validity that comes with an established group, and in so doing we effectively end the journey before it begins.”

The desire to “find the others” is vital. You do need people to support you on a new path. But if we mistake belonging for arrival, we risk getting stuck before we get started.

The second trap is trading one identity for another. As Rene Girard wrote: “Modern society is no longer anything but a negative imitation and the effort to leave the beaten paths forces everyone inevitably into the same ditch.”

Which is hard because of how many legible replacement suits are offered to us immediately upon leaving the default path:

The whole game of this phase is to avoid the ditch.

But I think avoiding the ditch for most people is impossible.

I went through a phase when I was pretty angry at my previous path. Why are the organizations led by all these people who love manipulating people? Why are they promoting the most political, not the most valuable? The system was broken, and early on, I wrote many essays trying to make my case!

Eventually, I saw it was a trap. Although there’s lots of money to be made selling coaching or products to people who want to escape, I saw it was not going to be “wise action” for me. I’d end up attracting people I didn’t want to help, and I’d be spending my time with similarly frustrated people. I knew I needed to process this frustration, accept it, and move on.

I think most people will spend at least some time in the ditch. The key is to know that this phase exists and resist all attempts to make it your identity.

The key to moving past this? Allow yourself to get lost.

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Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your god given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

On Monday or Tuesday, we’ll be receiving the notebooks so the team I’m working with at Otterpine can immediately start shipping the hardcover bundles people have ordered.

I decided it would also be fun to gift some of the notebooks for Black Friday. The only thing you need to do is pay shipping (US Only).

You can grab one here (discount automatically applies at checkout).

One issue: We can only do this in the US right now. We still have some work to do to set these up for international shipping.

Grab The Notebook

Also, I’m including all the digital editions of my books if you buy the premium hardcover

In addition to a free notebook and note cards, which are already included, if you purchase the launch bundle before Christmas, I’ll throw in digital versions of both of my books:

• PDF, EPUB, and Kindle Versions of The Pathless Path

• Audible code (while they last) and/or Podcast link to The Pathless Path Audiobook

• PDF, EPUB, and Kindle Versions of Good Work

• Spotify Gift code for Good Work (while it lasts) and/or Podcast link to the Audiobook

• And the PDF of the premium version itself.

Buy The Premium Hardcover - $95

I need to set this up on the backend but if you just email me your receipt this weekend, I’ll hook you up (also obviously good for previous purchases too).

Why am I doing this?

Bundles: The thinking behind a higher-priced book is that it helps reach the people who want all this stuff. Price discrimination: either you might want to support my journey, or you are just the kind of reader who buys 5 different versions of a book anyway.

Giving Stuff Away: It’s fun, and it’s always been part of how I do things. I started experimenting with alternative gift economy approaches in 2018.

Why Not?: I’ve been trying to lean much more into “what is the most generous thing I can do?” and “what is the most fun thing to do here?” Expect many more experiments along these lines in the future (and ideas welcome!).

21 “Pathless” Book Recommendations

I recently updated my “recommended reads” site for people on unconventional paths:

See Recommended Reads

That’s all for this week. I’m likely going to be dropping a few longer essays I’ve been working on for the holidays. Stay tuned!

-Paul

• I’m participating in this wise agency multi-part workshop with . It’s offered on a gift pricing basis, and you can learn more here.

• is hosting a multi-city “internet serendipity” tour. Pathless people will be at many locations, including Boston, DC, Austin, Seattle, Vancouver, SF, Denver, Miami, and Columbus: Register here

• I’m judging a writing competition with the . Here’s the prompt: Write about a moment when you (or a character) stepped off the expected road, or dreamed of doing so. What happened when you stopped following the map? Lots of cool prizes included, including a copy of my hardcover: see details here.

When Paperbacks Were Too Sketchy For Publishers

In the 1950s, paperbacks were not considered serious works of art by publishers and even some authors. Using cheaper paper and appealing to “lowbrow” mass audiences, paperbacks were the bottom rung of the literary hierarchy. Trade publishers were initially leery of paperback publication, “fearing it would cheapen authors’ reputations and cut revenues.” In a conversation I had with Eric Jorgenson, diving into the weird history of publishing, we both took a peek at what some of these “lurid” covers looked like:

Also, it wasn’t just publishers. Many authors also didn’t want their books “between the lurid paperback covers in favor of the 1940s and 1950s.” Some hardcover houses went so far as to include “the right to approve paperback covers in their reprint contracts.”1

Despite this, consumer preferences were undeterred. In 1947, approximately 95 million mass-market paperbacks were sold for slightly more than $14 million, but five years later, 270 million copies were sold for $40 million. By 1959, nearly 286 million copies were sold for $67 million, and “dollar sales of paperbacks exceeded those of hardcover trade books for the first time, even though paperbacks were much cheaper than hardcover books.”2

But the stance of seeing the hardcover as the only “real” book persisted, which basically meant less money for publishers and a bigger upside for authors. While his novel, Carrie, was purchased in hardcover for $2,500 in 1973, Stephen King’s writing journey really took off when he sold the paperback rights, one year later, for $400,000, to a completely different publisher.

This pattern repeats throughout history

In my research into the publishing industry, this pattern repeats throughout history:

1. Publishers look down on new formats (see paperback, ebook, audiobook, translation, and even merchandising rights)

2. Authors embrace them independently, profiting from them, or authors find ways to retain and sell rights after already having a successful book

3. Publishers eventually move to own and restrict more of these rights

If you want to publish a book through the traditional route, it is nearly impossible to avoid giving up these rights as an entire basket without investing in the book yourself or through a hybrid publisher.

Increasingly, however, this doesn’t make sense for the author nor the publishing house.

For the author, it’s clear why it doesn’t make sense. The authors care about being a viable creative person and making money from their work in any way possible. The publisher is not in the best position to actually execute on this. The publisher is great at packaging a book and selling it via traditional distribution channels. But even after 10+ years with ebooks and audiobooks, they appear to have no interest in doing anything creative with these formats or even pricing them competitively, let alone unleashing authors to make money using the IP and content despite many being world-class creative humans!

For a publisher, I think this is a weird self-own, too. In the age of the internet, a book is a meme, and the publisher should be interested in helping the meme spread as much as possible. But many publishers make it incredibly hard for authors to share their work. Unless the authors commission the cover or illustrations themselves, authors often are not legally able to take pictures of pages, pictures, images, or anything related to the book. They cannot remix the content, do interesting bundling deals, discount the ebooks and audiobooks over extended time periods, create interesting merch, or create alternative or high-end collectible editions of the book, like I did with The Pathless Path.

If I had sold the rights to my work, I never would have been able to create this:

a button to take you to the order page

This is a silly creative tax on our best writers

More than that, I likely never would have even thought about doing such a thing because as soon as I signed away all my rights, I would no longer be the creative director of my own work and likely would have lost motivation to come up with any ideas. This is a hidden creative tax on the most impressive writers of our generation.

The Pathless Path is clearly “working,” and as I interact with readers, I’m in a virtuous cycle of learning and playing with better ways of sharing and packaging my work. At scale, publishers have distribution advantages, but indie types can outcompete them with speed and experimentation. While these old companies still rely on the one, big, beautiful launch, I’ll be out here trying stuff, launching, relaunching, and having fun along the way, not needing to worry about the business case for any single decisions.

AI will expand the possibilities and real options of creators just like every technology has throughout history. Just this week, Amazon enabled AI-assisted English-to-Spanish translation. I already have some interesting AI-generated custom printed editions in the works for readers that I’ll share in 2026. With such cutting-edge technology moving so fast, I am excited to be in a similar position to King and others, retaining rights to capitalize on the upside of progress without needing to wait for a committee at a random company to decide that it makes sense.

I suspect this is why self-publishing, at least in the non-fiction tech/productivity circles I hang out with, appears to have hit a tipping point.

Self-publishing is having a moment in non-fiction

Interestingly, as I reflected on my reading habits, 90% of the non-fiction books I’ve finished (I’ve started many others) have been written by people who self-published. This happened without me being aware until I took stock last week.

While many popular non-fiction books are increasingly predictable, these books were weird, interesting, unpolished (in a good way), and thought-provoking.

Every time I write about this stuff, I get tons of messages from authors. This week, shared a reflection on his experience with publishing.

His story captures his own disillusionment with the industry, which started almost immediately after signing his book deal, Losing the Nobel Prize. He makes a trip to New York City to visit his editor at W.W. Norton. As he makes his way through the building, he finds that his editor’s office “was, in fact, the janitor’s closet. Broom, mop, cleaning supplies, and all.”

Early on, he faced pushback on his decisions. He had to fight for the title, eventually winning. But the publisher won, choosing their own image they preferred for the cover. In a weird twist, the publisher bought the rights from someone who didn’t own them and had to redo the cover. But Brian shares: “Embedded in my contract was a clause I’d barely noticed. Any new edition—paperback, audiobook, revised hardcover—required a new launch, new publicity, and a new book tour.” It forced a 2nd release, and the hype from the new launch enabled the book to take off.

What would have happened if they had never made the mistake? Would people have forgotten about it? Would Brian have stopped talking about it?

He pondered these same questions and had an awakening: “I used to walk past those grand Mad Men-appointed publisher lobbies and feel envy. Now I see them for what they are: monuments to a past that no longer exists.” He decided to self-publish his next three books and concluded, “The institutions you revere are more fragile, more arbitrary, and more human than you think.3

When I step back, I think this sort of waking up is happening to many more people working in creative fields, especially those who started doing their work online, and even more so for younger people who may not have inherited the scripts from the “old world.”

We need new plumbing to enable creatives

, founder of a very internet-first company, Kickstarter, has been doing some interesting work in this vein with his attempts to get an “Artist’s Corporation” (A-Corp) established in the US. It would be a legal vehicle for creators that would enable outside investment, payments, revenue-sharing, and even non-profit donations. His work on this made me realize so much of what we see as possible is downstream of the legal and financial plumbing of the economy.

Change the protocol layer, and you can shift the imagination of the participants of the system.

In a recent podcast with NPR discussing the idea, he pointed to the absurd status quo: “Artists are service providers who create assets that these larger enterprises acquire and capitalize on.”

With the internet, you no longer need to create raw material for bigger companies. You should own your own creations.

And do fun stuff like this.

P.S. The hardcover bundles are on track to ship by early December; we are only waiting on a container ship that’s carrying the notebooks, which is currently in the middle of the Atlantic. If you purchase the Medici tier, I’ll send you daily updates.

Here are some reviews from friends I’ve shared it with so far.

But first, a quick hardcover update

Sales of the new hardcover are going well.

We’ve pre-sold about 175 books to 20 countries now. Sharing the flags here because it’s kind of wild to see so much support from around the world!

🇺🇸 🇬🇧 🇨🇦 🇸🇬 🇹🇼 🇸🇰 🇷🇸 🇵🇹 🇳🇿 🇲🇺 🇯🇵 🇮🇱 🇮🇪 🇭🇰 🇩🇪 🇨🇭 🇧🇪 🇦🇺 🇸🇪 🇰🇷

And we’ve started shipping out some of the early copies to people who purchased the Medici tier, as well as people helping me promote the book.

The rest of the hardcovers are in port in NY, and the notebooks are en route from Morocco right now. Barring any logistics issues or global pandemics, we should be able to get these to people before Christmas (we can gift wrap and customize these with notecards, just add it in the comments of the cart).

I also shared an unboxing video this week:

If you’d like to check the book out or want to share it, check it out here.

Grab the book

Onward

#1 The appropriate amount of effort is zero

I love this essay from - it’s a simple but powerful idea:

There is an appropriate amount of energy required for each activity. Holding a cup, turning a steering wheel, or writing a blog post all need exactly the amount of energy that they need. This may sound like a truism, but if it were so obvious, why do many drivers often realise they are driving with a vice-like grip, with tension running up into their shoulders and jaws?

Let me share my slightly unusual definition of “effort”: it’s the felt experience of expending energy beyond what an activity requires, like tensing your brow when you try to understand something, or the excess tension in your hand when you hold your phone^.

Using this definition, it’s clear that the appropriate amount of effort for any activity is zero.

This doesn’t match with many of the stories we have about work and what’s worth doing, but if we accept this definition, where can you try less?

Read the full essay.

#2 You are not broken

had a great video essay on the aggressive hacks people employ in the self-help and creators worlds to hack attention.

In the video, he also highlights the pressure on creators to avoid anything even partially critical of other creators, especially those with large followings. This transforms the creative landscape from a space of healthy intellectual debate into one of transactional relationships, where people are always looking to “trade up” favors to people with bigger and bigger followings. This pressure is part of the reason I’ve scaled back my podcast and mostly focus on interviewing people I’m genuinely curious about.

This tension is a challenge, though, because it’s beneficial to befriend anyone who can amplify your work. If Oprah offers to cross-promote with me, I’d likely do it. Over the past couple of years, I’ve purposefully avoided this kind of favor trading with people whose work I don’t enjoy or tactics I don’t respect. Over the long term, I think this isa good approach because it means I’m sharing things I genuinely like and collaborating with people that inspire me.

Managing this is hard, and if you aim to have an audience for your work, you need to think about these kinds of tradeoffs. Many successful people are willing to grow at almost all costs, and so you just need to know what you are willing to do too.

One way I’ve leaned against the pressures is simply to write what I actually think. My essay on why you might not need to suffer and broader thoughts on the bad effects of hustle ideas and language have likely rubbed a few people the wrong way, people who could have otherwise “helped” me. But that’s okay because I stand behind the ideas.

Anyway, I appreciate Matt adding some thoughtful disagreement to the conversation.

#3 Jevon’s & Baumol

proposes a persuasive theory of how dual forces: rising costs from Baumol’s cost disease and abundance via Jevons’ paradox (tasks get cheaper, we consume more) combine to shape a new reality of work in the age of AI, not to mention political weirdness as our work realities evaporate:

In an interesting way, this hints at where Baumol’s will finally run out of steam - because at some point, these “last 1% employable skills” no longer become substitutable for one another. They’ll become strange vestigial limbs of career paths; in a sense. We have a ways to go until we get there, but we can anticipate some very strange economic & political alliances that could get formed in such a world.

a16z

Why AC is cheap, but AC repair is a luxury

If you live in the United States today, and you accidentally knock a hole in your wall, it’s probably cheaper to buy a flatscreen TV and stick it in front of the hole, compared to hiring a handyman to fix your drywall. (Source: Marc Andreessen.) This seems insane; why…

Read more

5 months ago · 181 likes · 25 comments · Alex Danco

#4 The housing theory of everything

This was the title of a good essay from a few years back. The takeaway was stark:

Western housing shortages do not just prevent many from ever affording their own home. They also drive inequality, climate change, low productivity growth, obesity, and even falling fertility rates.

Every young person I know, including those who have bought a home, has been talking about this for years. Among my friends, even those who were able to secure a home, there is a sense that the system isn’t quite working. On top of that, everyone sort of knows that many people are able to afford inflated prices with support from parents.

With the recent inflation and doubling down on restrictive housing policies (outside of rare places like Florida, Arizona, and Texas), this has led to some pretty wild shifts. While I’m a happy renter, I do wonder if I’d be thinking about my path differently if housing hadn’t become another speculative financial asset.

Check out the following charts I came across just in the last month.

Price-to-income is the highest it’s been in 50 years

Remote work kind of killed the retreat from cities?

Someone shared how remote work seems to have plateaued at 28%. While this is awesome and I love to see it, it’s certainly not high enough for people to be making permanent housing decisions to live in more rural areas. Most people know they have to be able to change jobs and have access to opportunities in a modern career, and knowing only 28% of jobs are remote (though this seems high?) is not enough to permanently reinvent, like so many were thinking of doing during the pandemic.

The median homebuyer was born in 1969.

Lots of people’s wealth is tied up in homes, and so it is political suicide to reimagine a different path. I suspect, however, that this cannot hold.

#5 Phone and kids

Emily Oster’s books are great for pregnancy and the first few years of parenting. She shared a nuanced but straightforward analysis of confusing data and hot takes from other parents.

She recently did a nice post on the impact of phones on kids. Here’s her takeaways:

• It’s difficult to definitively determine whether social media affects teen mental health because most of the studies we have cannot reliably show causality.

• There are tradeoffs to allowing your teen to use social media. Although the effects of social media are negative on average, there are people who benefit from it.

• Phones are a clear distraction in schools, and the evidence so far suggests that banning them improves learning.

• Regulation on social media age limits is unlikely, so it falls to parents to set boundaries. Much like teaching kids to drive, we need to decide when they’re ready for phones and guide them in using them responsibly.

#6 Books

I’m really enjoying the current reads:

• Breakneck by Dan Wang: Strong, clear, and interesting comparison between two modes of state planning, China vs. the US.

• Composing A Life: Just started, but a very good book recommended by that details four women’s different approaches for literally “composing” their lives

• Conscious Accomplishment: His new book is very good. If you’ve been someone who has gone through a work reinvention or gotten stuck on spiritual paths, this book is for you. I’m sort of blown away with how much detail Scott has managed to inject into his own journey from startup founder to someone who has a much better relationship with work and life itself. His idea of the “inner purgatory” described something I definitely went through from 2017 to 2019:

  “I call this period inner purgatory. Inner purgatory is the intermediate state between focusing on your inner work and feeling invigorated to take creative action in the world. When you’re in inner purgatory, you desire to accomplish things from an updated perspective, but find it inexplicably difficult. You may struggle with a lack of motivation, inspiration, or energy for external goals, despite knowing that you want more for your life than doing inner work all the time. Activities that once came easily may feel difficult. You may no longer feel like you have the same raw horsepower you once did. You can try to will yourself to push through things, but without the natural force behind you, you eventually exhaust yourself.”

Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing books and launching premium art editions of my book. If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs, and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your god given right, and there is plenty of other good stuff online.

A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.

I dropped an unboxing video of opening up my copy on YouTube. But today I thought I’d share some reflections on some of the doubts I’ve been struggling with over the last month.

Right now, a pallet of about 2,000 books, my specially designed hardcover of The Pathless Path, is sitting inside a single container, on a ship like this one, headed toward the US. Barring new tariffs, disaster at the high seas, getting stuck in a canal, or a global pandemic, they should be arriving in the US ready to ship out by Christmas.

In the run-up to the launch announcement last week, something I delayed for more than ten days, I wrestled with lots of self-doubt:

• Will it flop?

• Did I spend too much money on this?

• Should I have done something smaller and quicker?

• How did I spend this much?

• Am I charging too much? Not enough?

• Do people really want this?

Before this project, I’d kept all my projects simple: minimal upfront investment, bootstrap, work independently, and focus on staying profitable and cash-flow positive. With this project, I invested a large amount of money upfront, kept it mostly secret, and am announcing it as part of a major launch. I designed previous projects to quit, but with this, there is no clean off-ramp.

Despite this, as the launch announcement approached, especially after some critical feedback on the pricing, I started doing mental gymnastics, manufacturing a narrative that would give me an off-ramp, a way to say to myself, “This is fine!”

If I make back 20% of my investment, I think I could be okay with that.

I’m going to be selling this for years; any short-term outcomes don’t matter.

This is part of a larger bet and pivot; it will take time to fully develop this. It would be okay if I only sold about 20 books. I can think of it as a branding exercise.

Why are we like this? Why am I like this? I mean, seriously. Meta has burned more than $70 billion on VR bets, and I’m worried about a loss of low five figures!

Maybe these stories are right and useful, but in creating them, mostly what I was doing was resisting my own feelings.

I am nervous, afraid of looking silly, and might actually lose a bunch of money on this, and all of that is actually okay.

Deeper than this is something scarier to fully feel: I care.

I care about this book as a creative artifact and as an expression of myself and what I believe. I created it because I wanted to lean against the creative compromises that too many people make and the hyper-efficient spreadsheet logic that pervades our broader culture. Even simpler, I just wanted it to exist.

As I prepared for the launch, building out the landing page, and getting feedback, I lost track of these deeper motivations. And even though I’m not in any real financial danger and have funded the investment out of cash flow from book royalties, the idea of not at least breaking even stirred up gnarly money emotions.

It’s almost as if my subconscious dreamed up this project to test me.

You should never waste money. Never take risks.

These scripts were installed early in my life, as they are for many of us, and of course, they were useful. They helped me invest wisely, understand personal finance, and enabled me to quit my job without a plan. They also helped me easily shift into extreme frugality while not making much early on my path. But they also aren’t needed anymore. The lessons have been learned. I’ve made it to 40, never letting myself get close to financial danger. I can trust myself and trust the automatic fears a bit less.

But letting go of the scripts that shape much of our behavior early in life can be hard. It wasn’t until my thirties that I stopped seeing work as something that involved suffering. And once I let go of that, I discovered money scripts, which seem to be rooted at a deeper level in the body, the final boss of personal growth.

To let go of these money fears isn’t just being stronger or bolder or more courageous; it’s actually increasing the faith in the world that everything will be okay. For so long, a reliable mode of trusting the fear worked. But I know it’s time to see if other things can work too. This is the frontier worth exploring.

After basking in all my beautiful anxieties for a few days, I finally started writing. As soon as I started this essay, I relaxed. As I wrote, I remembered that this is the place where I can slow down and make sense of it all. I reflected on how much I love this, right now, this writing thing. And further, that a principle from the start has been that my creative work isn’t for anything. Because even when I try to do things for something else, I lose myself, drift into cynicism, and sell out my energy.

The creative work is the win.

The Pathless Path was about leaning against the pressures of the world and creating the freedom to do work that matters, no matter what.

This, I had to remind myself, is what I am trying to do with this book:

The other thing I’ve realized is that on the other side of this tangled knot of emotions is usually unfelt excitement, and as I’ve finished the creative work of this book and moved onto the prep for sharing and marketing it, I’ve been spending too much time in worry about what might go wrong and not enough in what might go right.

When I launched The Pathless Path, I literally couldn’t imagine any of what eventually happened with the book. My “best case” scenario was breaking even. This is a recurring pattern on my path; I’m almost always more focused on limiting downside than thinking about any potential good things that can happen. Again with this launch, I was falling into the same pattern.

Ultimately, in writing this, I realized that my doubt is a blessing. As my friend Lawrence Yeo writes, “If you had no doubts whatsoever about the work you’re doing, it likely means that you don’t care enough about it.”

On my previous path, I didn’t really care if we lost pitches or didn’t do our best in a client meeting, something my Senior Partners didn’t always appreciate.

Now I care, and it’s annoying as hell.

But it also means I’m moving in the right direction. I know it’s going to be a lot of fun once people get this book and start sharing their thoughts with me. And since the first couple of people have seen the book, it reminded me why I decided not to de-risk the project by printing a smaller amount, doing a long pre-sale, or raising funds first through a Kickstarter. That would have been the path of resistance.

I wanted to print a bunch, fund it up front, and put it into the world, on my terms, as a test to see what it might feel like to do something from a sense of abundance. The mantra I kept repeating throughout the project was assume success. Why? Because it’s the opposite of what I’ve always done. Scary? Sure. Potentially financially embarrassing? Also maybe.

But what is the point of this path if I can’t take risks, try bold things, and push my own capacity for growth along the way?

The first ten days of sharing this out in the world have already been exciting. I’m feeling drawn in a number of interesting directions. I’m seeing lots of possibilities for the next phase of my journey. I can also feel the genuine excitement, passion, and care I have for my work and see how it’s showing up in my life

I want to stay on this path, and I want books to be part of it.

I wanted this book to exist. And now it exists.

Isn’t that cool?

Quick Sales Update: So far, people from 20!!! Countries have purchased the book, and including gift copies, about 200 copies of the book are spoken for. This, again, has exceeded my expectations. So thank you again for supporting this!

check out the book

Also a couple of people have asked about buying bulk copies either to gift or offer to their community. I’m happy to offer a small discount and we can even handle the shipping on our end. Just

I’ve gotten a lot of questions about how something like this came together, so in the spirit of sharing, I thought it might be fun to share the behind the scenes.

A quick note: This e-mail has a ton of pictures, and will likely be clipped by Gmail or others, so it might be easier to read the whole thing in your browser.

Read On Web

It’s April 2023.

I just turned down a two-book deal from Penguin. I shared that story last week.

Long story short, after walking away I knew I wanted to make a bet on self-publishing and do something weird, creative, inspiring, and bold.

The wheels start turning. I start reaching out to people doing creative things, like a friend at Stripe Press and others.

It’s August 2023.

I’m sitting in a Zhongshan apartment in Taipei and talking to Saeah Wood. She understands someone like me who must do things their own way, well, because she’s wired like that too. She founded Otterpine to help indie authors like me create beautiful books. I’m excited talking with he and she’s somehow the first person I am talking to in the industry who still seems inspired and creative, doesn’t make creative compromises, nor does she obsess about marketing tactics.

The fact that she handles all of Derek Sivers’ books is a plus, too. Derek’s been directly selling his books for years and doing it in his own way. He’s one of many inspirations for this project.

I also share my concerns. I tell her I’m worried about the budget. I’ve been very bootstrapped in almost everything I’ve done for at least seven years. She pushes me, telling me it will be expensive, but it will be worth it.

March 2024

I delay taking action. Afraid of actually investing money out of my own pocket. Struggling to find a work flow after becoming a dad.

But I can’t let go of the idea.

Saeah pings me. “We have availability for a new client. I’d love to work with you.”

In 2023, I made way more than I spent. I decided that I can mentally use some of this “surplus” for the project.

I put down a $1,000 deposit. The wheels are in motion.

Spring 2024 - We start brainstorming

We start slowly, brainstorming ideas. One of the biggest inspirations for the book was the Steel Brothers Walden book that my friend sent me.

Some people feel mimetic desire for others’ possessions. I instantly felt mimetic desire for the state of being able to create something like this:

The text on the cover also excited me, and I mocked up something for The Pathless Path. Here is my very bad, hacked-together Figma mockup I sent to Saeah.

I also started sharing other sources of inspiration

• I love what fantasy authors are doing with special editions like Brandon Sanderson

• Craig Mod’s books are inspiring and well-designed

• Stripe Press has amazing covers and clearly cares about books

• And some others that integrate text into covers

Beyond the cover, I’m also inspired by various people’s experiments over the years. Some notable projects worth mentioning include:

• The Steel Brothers’s Walden Book

• Kevin Kelly’s expensive and very heavy art books of photos from Asia

• All of Craig Mod’s writing and art book experiments

• Brandon Sanderson’s leatherbound books and kickstarter bundles

• Ryan Holiday’s leatherbound version of the Daily Stoic

• Gretchen Rubin’s notebooks

• Baron Fig products and design asthetic

• Stripe Press books and websites

We start doing the cover first. This will help us pick a direction

We start with the cover. Here are a few very early mockups:

I don’t love any. The lines and foil print are intriguing, but the only ones that make me excited are the ones with hand-drawn illustrations.

In this phase, I’m trusting my intuition. I want to feel an immediate “of course” sensation flowing through my whole body rather than “this makes sense.” I felt it when I saw the original cover of The Pathless Path.

I’m not feeling it yet, so I asked them to keep going with the illustrations.

The good thing about working with a great team is that they can take my mediocre “I don’t really like this and that” feedback and come back with something beyond what I could ask for.

The illustrator, Elizabeth Evey, comes back with this, and it blows me away.

Whoa. This is nice. The illustration with the cloth cover was exactly the vibe I was looking for. The scene depicted was one we brainstormed around the scene from the “pebble in my shoe” alive (h/t ). Eventually, I decide that the pebble in the shoe scene isn’t right for the cover. I want to make it less about a moment of discomfort and more about wonder and taking the first step toward new possibilities. You can see some of the details we changed in the final version. In addition, here’s the back cover quote we landed on, one of the most highlighted and shared quotes from the book:

ok no more, ready to buy

Then we focus on the inside

“We will do the font and layout test next.”

The structured process is helpful for me, because when it came to the inside, I didn’t quite know what I wanted.

I talked about clear, bold colors and simple images. Here are some of the initial versions we whipped up:

These were all a bit too intense for me, which was useful, as I then started to develop a strong and clear point of view about what I liked and didn’t like.

I started to focus on the following:

• I wanted simple and bold. I didn’t want a complex mixing of multiple shades

• I tend to gravitate toward blue, especially the bottom one

• I didn’t want any overly complex drawings or graphics

• I loved the full-page quotes

From there, we decided to do one or two blues, on cream pages, testing some of the following colors

I ended up really liking this dark blue:

I didn’t love the 2nd shade of blue, and we tried dozens of shades and ultimately decided to keep it simpler and stick with only the dark blue.

This ended up matching really well with some of the illustrations we were doing. A few iterations later, we ended up with something I loved: clean, simple, and clear:

two clicks from here and this is yours

Content + Editing

A Foreword

I reached out to Ali Abdaal last year and asked if he would consider writing a foreword for this version of the book. I was nervous asking, as I just generally am still not great at asking for support. But I’m glad I did, as he was excited to do it. I think his contribution adds a nice story to kick off the book as he found permission from it to leap from medicine to full-time entrepreneur.

Author’s Note

It’s been almost five years since I started writing this book in December 2020. A lot has changed since I published it in early 2022, too. I wrote a short reflection on becoming a father on this path, my continued enjoyment of the journey, my surprise at the success of this book, and my future aspirations. It was really fun to reflect on how this book has been such an important part of my life over the last few years.

Full-Page Illustrations & Quotes

There are at least seven full-page illustrations throughout the book, and many more small touches throughout the tie in with the images.

Here is one which I love:

And another one:

And a few of the 30+ quotes from myself and others from the original:

purchase to get all the quotes

Some Light Editing & Design

While the book was completed years ago, I still had Otterpine’s team give it another proofreading pass. While we didn’t make any major changes, we improved the consistency of things like spacing, em dashes, spellings (toward versus towards and how we used footnotes and captions. Also, by creating the quote pages, we moved many of the quotes out from the start of chapters which improves readability.

I also used their suggestion of going to the indented spaces over blocks, mostly because I liked how it looked on our designed pages and I’ve grown more friendly toward it as I’ve read more fiction.

I also took their edits and cleaned up a bunch of stuff in the other versions and have launched these as “Version 2.0” of The Pathless Path. For now, the updated author’s note and foreword will only be in the special edition hardcover but I may update everything for the books 5th year anniversary in 2027.

An index + bookmark ribbon

The book has a ton of references. Now there’s an index at the back.

And a helpful bookmark ribbon to help you mark your favorite page.

And A Few More Things

I signed over 2,000 copies. We have about 1800ish that made it to print

This was a bit tricky to pull off as the book was being printed in Italy, the books are being shipped from the US, and I am living in Asia. Signing 500 pages a day in a coworking office in Thailand was more complicated than I expected, my signature evolved daily.

A slip cover

Adding a slip cover was expensive, adding a bit of additional cost to the book, but we brainstormed a little slot in the slip cover that matched well with the illustration.

I thought it was a fun idea, and I decided to go for it. This will likely only be a first edition thing, so if you like slipcovers, definitely grab one now.

Note Cards

We created a pack of five quote notecards with every order. These are nice, thick cards you can use to send mail or just create a very fancy to-do list. These are much higher quality than I expected too. I got a pack of these last week. Really nice.

A companion notebook

We made a simple notebook along the same lines as the book that has a couple of new quotes and some playful touches. This wasn’t as much as the slip cover, but I decided to do a bigger print run of 5,000 of these to sell on its own in the future and hopefully gift in other creative ways.

Packaging

All early bird bundles pre-ordered before December 1st will be individually gift-wrapped and handled with care. If you order, you’ll receive something like this:

Inside the wrapped package will be a shrink-wrapped book, the full notecard pack, and a notebook. In addition, you’ll get a handwritten card that we can customize for gift giving or your own entertainment.

This should make for some pretty incredible gifts. Just think about giving this to your parents who have been giving you a hard time about your life choices, or that VC in your life that keeps telling you to grind harder. Nothing changes hearts and minds like a delightful gift!

This packaging and premium shipping definitely add quite a bit to the cost as well ($7-$10 a book), but at least early in this process, I want to give everyone who takes a chance on this a premium experience.

Distribution

For now, we are focusing on selling direct, through Shopify, and via a single warehouse in North Carolina. In the future, we will explore other channels like selling through Amazon FBA and alternative distribution if demand increases, especially abroad. We’re also going to explore specialty shops, or independent bookstores that may want to carry something like this (if you are at Pier 1 hit me up!).

But for now, I’m keeping it simple and learning as we go.

The Economics Of This

TL;DR: I’m not sure if this will be profitable, but there is a long-term path to making money selling more of my books directly, packaging them with other items, and continuing to learn and improve. This feels fun and exciting for me,

For the last 8+ years, I’ve had an extreme bootstrapper mentality. Early on, I struggled to spend more than $100 on anything I’d create. Even though creating online does mean spending money and paying platform fees, I’ve had 70-80% margins for the first six years of this indie path. Investing in this project meant that those margins were closer to 50% last year, and this year, it may be much lower because I’m frontloading most of the costs.

The total investment upfront is going to be somewhere in the $75,000-$85,000 range, and it will depend on final costs, shipping, and other fees of the books and notebooks, which are still being finalized and need to be shipped to Otterpine’s warehouse in North Carolina. My goal is to attempt to approach breakeven or even profit at around 500-1000 books. This will be hard, but it will also enable me to shift more quickly to different creative pricing and bundling options in the future.

Ongoing costs will also add to ongoing costs, and this is the reason most self-publishers just stick with print-on-demand and digital books. Because Otterpine is managing warehousing, there will be fulfillment costs, shipping costs, lost package costs, unexpected customs fees, which we may not be able to predict, and packaging costs on top of printing and production. We’ve already had a minor issue with the notebooks being delayed and may have to incur an extra shipping fee, but it still should be ready by Christmas!

Because of this, I created a few tiers for people who want to support this project in a slightly bolder way, including the “Medici tier”, which includes an hour-long call with me.

One person who saw the book early last week said, “This was the best book receiving experience I’ve ever had”. Epic. That was the goal.

All of this is to say that this project was a huge bet for me, and until I launched it was quite scary. But now that people are ordering (I hit over 100 orders this weekend!) I am feeling much better.

What is this path if not for doing interesting things and actually using some of the money I make to take risks and create things in the world?

Credits

So much credit goes to Saeah Wood, who was a great co-creator throughout this process. She guided me through creative decisions, money freakouts, and helped me to dream bigger. She’s also built an incredible team. Every time she said, “We’ll come up with something awesome,” they delivered.

The whole Otterpine team (learn more about them here)

• Creative Director & Production Manager: Saeah Wood

• Editorial Manager: Amy Reed

• Design: Ivica Jandrijevic

• Illustration: Elizabeth Evey

And other shoutouts!

• Original Editorial: Paula Trucks-Pape

• Author Photo: Alicia Tsai

• Printed in Vicenza, Italy

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ok take me to the book

TL;DR: I’m launching a premium hardcover book. It looks like this and I created it to inspire and delight. You can also read the full essay on my site, or go check out the book directly here.

“Okay, what’s your plan for my book?” I ask.

I’m on a call with a top imprint at Penguin Random House. An editor had reached out a few weeks earlier to “discuss future projects,” after my self-published book, The Pathless Path, started climbing the charts. In a quick call, she said she thought their team could help the book reach many more people. While skeptical, I accepted her invitation to another call, this time with the senior publisher and lead editor.

I pop onto Zoom. Three people are waiting. They seem in a rush. After a short round of intros, they cut to the chase: “We want to get The Pathless Path to more people. We know how to do it. We’d take it out of print, redo the cover, and update the content.”

This throws me off.

Hmm. . . People are buying this book right now. I’m literally selling thousands of copies a month right now. Why take it out of print? Also, I love the cover.

We keep chatting. They detail why I will struggle as a self-published author. I’m slightly annoyed but open-minded.

“Okay, what are some of the ideas to reach more people?”

“We like this book a lot. We can send preview copies to authors we work with, like (redacted).”

“I mean nothing’s stopping you from sharing it with you now,” I jokingly say.

“Nice try.”

(silence)

“Ummmm, any other ideas?”

They don’t seem to have more. They are thrown off that I’m not jumping at the offer. While it’s no question that they have much better distribution than I do, I thought they’d have at least one idea related to the themes in my book.

“Look, this is a really good offer. You should take it. It’s good for you. Your book will reach many more people.”

But it doesn’t seem like a good offer.

Caring Is Incidental For A Business Case

To a publishing company, my book is one line in a massive database of titles. Their game, if I handed it over, was to see if they could turn it into a cash-flowing perennial seller. If it didn’t take off, they’d move on.

To me, the book is a significant creation. It is more than a line item. Through writing it, I stepped deeper into a portal for a different way of being. It isn’t a business card for further opportunities. It’s part of my life, an expression of something deeper, and now, a part of my readers’ lives too.

Writing The Pathless Path also unlocked something in me. It helped me admit that I care deeply about my work and I care about how I do it.

To them, my level of caring was an incidental factor, not one that be part of a business case for acquisition. On the call, it was obvious that a team publishing hundreds of books each year could only care about my book so much. It’s not their fault, its the game they have to play.

Even more simply, the math didn’t math. In the month before the offer, I made $10,000 in royalties on 2,000 copies. By the time I talked to the full team, sales were inching even higher, which made a $70,000 offer for lifetime copyright plus 70 years after my death easy to reject.

Before the call ends, I can tell they don’t like the fact that I am not enthusiastic. They push me to tell them what would make me interested. I haven’t thought about it in detail, assuming they won’t negotiate.

“I don’t know. Much higher,” I respond.

“Okay, tell us.”

“Okay, ummm, uhh…I’d be more open to selling the rights to only The Pathless Path and not including a future book. But I think the book has a lot more potential than your offer implies. At $600k, I might be interested.”

As soon as I say that number, the energy drops to zero. They are shocked. They think I’m out of my mind.

They tell me I need to talk to an agent.

The call ends, awkwardly.

I sit there for a few minutes, thinking, “What was that?” Eventually, I get up and walk into the kitchen. I tell Angie, “I’m definitely not doing a deal”.

But in the days after the call, I feel great. I am fired up. These were the people who were the best in the world? They wanted to take a book people loved and take it out of print? And they wanted me to sign over lifetime creative control after only a 30-minute call? It all felt like a weird dream.

None. Of. This. Makes. Sense.

Still, I needed reassurance that I wasn’t being reckless. I texted my writer-friend David Perell, who lived nearby: “Yo, I just got a publishing offer, and I’m likely going to turn it down, but have no idea what to think about this. Can we go for a walk?”

Along the Colorado River in Austin, David and I started walking.

I get right to it: “Am I crazy, or does this industry not make any sense?”

David had been running the online course Write of Passage over the past few years. His course had attracted thousands of people. Like me, he had embraced the power of the internet, connecting with and helping a group of people on unconventional paths.

David saw traditional publishing through a similar lens. The prestige these institutions offered was overpriced. And certainly, almost nothing was worth selling out our most valuable asset: creative passion.

He pushed me to dream bigger: “You are still early. All my students love this book; I hear people talk about it every week. You should double down on it, just like you talk about in the book.”

On the call with Penguin, I hadn’t planned to make a counteroffer. When I threw out the $600,000 number, I shocked myself, too.

Really, it was a first step in acknowledging that I did, in fact, have a hit, and it was worth continuing to invest in. At that moment, a fire was lit inside of me. I needed to be bolder. I needed to keep going forward, in my own way. If the industry wasn’t going to obsess over the details and care about the book in a way that felt right, then I would do it myself.

The Publishing Industry Isn’t Broken, But it Sometimes Breaks People

I wouldn’t have lasted ten years in strategy consulting if I didn’t enjoy a deep dive into the structure and incentives of a new industry. So, for the next few months after declining Penguin’s offer, that’s exactly what I did, guided by simple questions:

• What’s the deal with this industry?

• Do the traditional publishers still matter in a digital age?

• What is so powerful about the combo of prestige and a modest one-time advance that convinces authors to relinquish lifetime creative control over their most important work?

My conclusion: The book industry isn’t broken. At a high level, the industry is growing. Online sales and digital formats are booming, and self-publishing has opened the door for more writers to write books and build a career than ever before.

When people say the industry is broken, what they are really pointing to is the publishing houses in New York City still running a 1960s playbook. They keep ebook prices high, dismiss self-publishing tactics, resist print-on-demand, and limit authors’ creative input and rights. When authors do obtain alternative arrangements, like Hugh Howey, publishers don’t take the opportunity to compete or take the chance to make more money; industry insiders beg each other to maintain the status quo:

Practically, these companies are “working.” They generate steady, reliable cash flows for conglomerate owners, excel at a playbook for certain kinds of books, and offer prestige and credentials that still matter to many. These companies will keep chugging along as long as passive backlist income keeps flowing, which can be up to 70% of revenues for some companies. To paraphrase Upton Sinclair, “It is difficult to get anyone to change when the business model means there is no incentive to do anything different.”

Employees and agents have emailed me lengthy complaints in private, acknowledging a strange code of secrecy that seems to pervade the industry. This seems to extend to authors, too, who play along, afraid to share royalties and deal information. Their messages are always the same: They entered this field because they genuinely care about books, yet the system makes it nearly impossible to do so. Many people leave a burnt husk of themselves.

, author and head of Infinite Books, details the state of the industry: “The problem is there’s been so much consolidation and there’s just less room to take risks. If you have a bunch of books that aren’t successful, you’re costing the publisher money without having a return.” This means each book has a short window to prove its worth. As Jimmy adds, “The entire business model is predicated on your book being a hit within the first two weeks. If it’s not a hit within the first two weeks, publishers sort of give up on it and move on to the next project.”1

This Creates Unnecessary Cynicism at Scale

I’ve never encountered an industry as cynical as the book industry.

The closer you get to its orbit, the more you start to hear several phrases repeated as if they are trying to convince you to join a cult: Don’t worry about control over your work. Trust the agents and publishers; you can’t negotiate your own deal. Of course, you shouldn’t expect help with marketing. Sure, the deal is not good, but everyone signs the deal. Publishers know “the market” better than you. Just sign the deal. Take the money. Self-publishing is for losers.

Here are only a few things authors who have participated in this system have said to me privately over the last couple of years:

• “I didn’t come close to earning out my advance, so it’s worthless to ever talk about my book.” (at least 4-5 authors in some form)

• “I hated the cover, but I just didn’t want to fight them anymore.”

• “I hate the subtitle of my book, but they wouldn’t compromise. Sadly, I am just less enthusiastic about promoting it now.”

• “I’m shocked at how quickly they stopped responding to my emails and caring about my book. I wish I could get back the rights.”

• “I’d love to do a spinoff, smaller book, but I can’t do anything related without asking for permission first.”

• “As soon as it was clear the book wasn’t going to take off, they moved on.”

The publishing industry takes the most ambitious, creative, and driven writers, extracts their exuberance, and replaces it with cynicism. Writers become “authors” who focus less on the craft and more on gaming the system, becoming agents for these faceless conglomerates.

I’ve seen even the most principled and determined authors get sucked into this vortex. I hate to see it, but I also know incentives matter. The system is getting what it wants.

Creative work should inspire more creative work, but the industry doesn’t seem to feed that cycle. Instead, it inspires bigger and bolder attempts at the same playbook and generates creative pollution in the form of cynicism.

In an era where writers literally have direct access to the means of production and a direct way to reach readers, we can push back against this. We can raise our standards. We can invest in the direction of creativity instead of PR. We can say no to deals that risk undermining our creative fire. We can retain our rights. We can take risks that might not work.

We can reclaim the book.

To Reclaim the Book, We Must Care About The Book Itself

A friend once told me that he felt the pressure to write a book from a young age. His grandmother was a best-selling author, and his parents also wrote books. Finishing a book was how you “made it” in his family.

I had no such pressure or expectations upon me when I set out to write a book. To me, it was a fun extension of what I was already doing, publishing words on the web, mostly to friends and fellow curious humans. It was an advantage not knowing anything about doing a book the “right” way. By crafting it in my own way, I injected my own weird quirks into it. I structured it in ways that would horrify most non-fiction editors, moved through references quickly, leaving the rest up to readers, and refused to tie my ideas into a bow with prescriptive frameworks.

It wasn’t supposed to work.

Two people with publishing experience warned me against shipping it.

It wasn’t ready, they said.

But it worked.

The history of publishing is filled with such eccentricity, and it’s where we should look for inspiration.

One example is William Morris, who founded the Kelmscott Press in the 1890s and vowed to push back against the uninspiring books of his day, amidst the rise of mass production. Morris was obsessive and opinionated, with strong perspectives on paper, typography, and the spacing of words, lines, and text on a page. He studied the calligraphy of the Middle Ages and the typography of incunabula, early printed books from before the 1500s. He designed his own typefaces, including Golden Type, Troy, and Chaucer, which he created specifically for Geoffrey Chaucer’s works. While many of his projects were unprofitable, many of his books are now seen as masterpieces of the era.

He felt that, behind building your own house, the book was “Perhaps the most satisfactory work of art one can make or have.” In more direct terms, he told an interviewer for Bookselling in 1895, “I felt that for the books I loved and cared for there might be attempted a presentation...which should be worthy of one’s feelings. That is all. The ideas we cherish are worth preserving, and I fail to see why a beautiful form should not be given to them.”2

In today’s age, as soon as you snap out of the spell of the traditional publishers and look around, you do notice inspiring experiments.

Stripe Press clearly cares about books. Infinite Books and Jimmy Soni are entering the industry with an author- and tech-first mindset. James Clear helped launch an authors-first hybrid publisher at Author’s Equity, and the authors I talk to love working with them. Bookvault pairs beautiful design with print-on-demand flexibility. Lulu gives you an API to print & ship books anywhere in the world. Craig Mod has nearly a decade of putting art and craft first, publishing beautiful art editions of his work. Derek Sivers sells direct and only makes authors pay for his books once. Steel Brothers is turning books like Walden into breathtaking collectibles. MSCHF is remixing reality itself with its releases. Even rogue divisions within Penguin’s imprints prioritize design, like their clothbound classics.

My Contribution

For the last 18 months, I’ve been trying to channel my inner William Morris, creating a book that expresses the care and passion I have for the ideas in The Pathless Path. It’s a significant investment, and the most I’ve spent on any project by a 10x margin in my 8+ years as an independent creative. It’s a bet on beauty, a bet on books mattering, and a bet on caring in a world that is not optimized for caring.

Throughout the process, I trusted my creative impulses while ignoring MBA Paul, who kept trying to force rational creative compromises. I listened to my gut, made several bold decisions, and ended up creating something delightful. From the start, I decided I would price this book as a premium product, giving me space to push the creative frontier to an extreme level. This is why the book will launch at $95. The early copies will come with some extras, but the book will remain priced as a premium product. If you want the other editions, you can grab the Kindle for $4.99!

A big motivation is to challenge the idea that a book is just a fancy business card to market other services. The internet means we can skip the gatekeepers and their need for mass standardization, offering many more variations of a book. Authors like Craig Mod and Brandon Sanderson have shown that there is demand for premium books and that readers are eager to support indie authors. I am convinced this trend will continue and I want to nudge the future in this direction. While I don’t have as impressive an audience as people like Craig and Brandon, I am someone who must move in the direction of my beliefs. All of this is a bit scary, and while some people have already told me that this is a ridiculous price to launch and sell a book, others have told me I’m not pricing high enough.

Ultimately, some lack of interest is a good thing. Like most of what I make, it isn’t for everyone. It’s for people who want to back a project like this and also encourage me to dream bigger, run more experiments, and bring others along, all while giving other writers permission to reimagine a writing life in today’s age.

You’re also getting more than a book, and this is hard to convey in words. As one early recipient of the book texted me: “This new book layout is SEXY…really really really well done.” When you open up the nice package we’re going to send you, you aren’t getting words on pages. You’re getting the full force of my creative energy flowing out of something impossibly beautiful and different. You’re getting something that feels special and will delight you.

If we are to reclaim the book and the entire ecosystem around books, we must not treat it like a commodity in a massive global supply chain.

We must take it seriously.

This is what I’ve tried to do.

I don’t know what happens next, and that’s okay.

But as I end many letters here, I’m excited to find out.

It’s time to reclaim the book

You Can Buy It Here

Or share this essay.

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I’ve also put the page on my website if you’d like to link to it there: Reclaim The Book

1

How I Write

Jimmy Soni: Kobe Bryant's Secret Obsession with Writing

Jimmy Soni has listened to 400+ interviews with Kobe Bryant over the past four years. Turns out, Kobe wanted to be the next Walt Disney after basketball, so he obsessively studied storytelling and wrote every day for 15 years…

Listen now

8 months ago · 16 likes · 4 comments · David Perell

Last week, I did a book talk in Hong Kong with follow by a meetup. It was really fun to meet people, especially in Asia, who are exploring alternative paths. Then this week, I did an event followed by a meetup in Taipei, which was extra special. I never imagined I’d be promoting the Chinese version of my book when I was writing it in Taiwan in 2021.

In addition to the event in Hong Kong, Ali and I recorded a conversation about the process of quitting your job. Both of us have gone through reinventions over the past ten years, leaving prestigious careers to do ideas on the internet. Over the years, both of us have heard countless objections and roadblocks people have faced, and so we sat down and talked through them.

I’ve noticed that the people who actually do make a change in their work trajectory all have one thing in common: they were able to replace a default story about what they should be doing with an alternative story. When it comes to the act of quitting and trying something new, people almost always have some story related to money.

As I’ve jokingly said, money is like the final boss of self-reflection. It’s the place we hide our deepest insecurities.

In terms of taking a leap, I’ve been playing around with an idea I’m calling “leap capital.”

Leap capital is a specific quantity of money or other resources and an accompanying story that someone uses to convince themselves that it is reasonable to make a change in their work life.

It almost always shows up in the following formula:

I have X, which means it’s reasonable to take risk Y for Z period.

X is the leap capital. It can be an amount of money, a level of wealth, or even a recent change in income or wealth that convinces you that it’s reasonable to make a change in your life, either temporarily or permanently.

After graduate school, I had some long-term investments but also $70k in debt. It felt unreasonable to do anything except continue on my path. It wasn’t until I paid the debt off and started building savings that I thought about anything other than working full-time.

When I hit $50k in savings, something shifted. Part of it was the reality of growing my savings each month. But the deeper shift was that I was starting to do the math. With some small reductions in spending, $50k in savings represented a year of living expenses. This quantity of time, a year, felt important. I don’t know why, and I don’t have a detailed model of the math behind it. It was arbitrary but also personally persuasive.

As I started dealing with some stressful situations at work and contemplating the fact that maybe jumping to my sixth job wasn’t the answer, I started playing with the idea of “testing” a freelance version of my current path.

Hmm, one year, I could make that work, right?

When I quit, I didn’t think past a year. I wasn’t quitting forever; I was just going to test the waters for twelve months. Even though I was scared, this felt reasonable. I felt safe. The worst case was that my savings would go back to where they were only a couple of years earlier. I could get a job again and move on.

For some, $50k is not nearly enough. One guy told me straight-faced that once he had $10 million, he could finally take a break to write the book he wanted to write. Another tech guy told me he would only quit once he fully replaced his $300k tech salary via a side gig. Others need less, like , who quit her job and traveled for a few months with only $7,000 to her name.

We all have a unique relationship with money. And what feels reasonable to one person often feels terrifying to another. The important thing about these stories is that they help you arrive at a feeling: I am not completely reckless.

This feeling, rather than spreadsheet reality, seems to matter a lot more for people in being able to leap.

There are many examples of this:

• Months of expenses: shared that, “For me, it was monthly expenses *12 for a year-long sabbatical, and I multiplied that by 2 again just to feel extra safe. It also helped that I never expected to save growing up, and I wouldn’t have, if I had never left Turkey, so it felt like an extra that I could spend.”

  • One feature of the months of expenses approach is that it sets a clear deadline: “This is when I will run out of cash and need to change my plans.”

• Side gig income: “I’m making $2,000 a month from a side gig right now.” For some people, this is enough. It’s proof that this alternative path has potential. For others, they need to match their current salary. Anything less is failure or brings up too much insecurity or guilt.

• Net worth: “I’m worth $2 million, that seems like enough to take a risk.” What I’ve found interesting is that people using this approach often don’t run the numbers. They care much more about total amounts. If they had run the numbers, they might have realized it wasn’t quite a big risk to take a year off when they were at $1 million. Regardless, net worth has become increasingly important to many people, and hitting a milestone can help some shift stories.

• Paid leave: shared that “My leap capital came from becoming a father - California paternity leave covered our family’s minimum expenses for 12 weeks, which gave us runway to be more creative and contemplative.”

• Unexpected earnings / one-time sum: Like Sinem above, when some people earn more than they expected, they view the money as permission to do something different in their lives. Other examples of this include receiving an inheritance, making an investment, or winning a grant, such as the O’Shaughnessy Fellowship. For some, an unexpectedly big bonus can serve the same purpose:

  • shared that during the first year of COVID, she started thinking about leaving her job: “I finally hit my breaking point in November of 2020.” What made the choice easier was that her company “had the first good sales year in a while.” She was due to get about “4 months of salary” as a bonus in March 2021. "So for 4 months, I had to keep my mouth shut, not get fired, cash my bonus check, and only then put in my notice.” To her, the four months meant time to figure this out: “I could take the summer to get clients, take a break, or otherwise figure out my next steps. It meant I could leap without a total plan in place.”

• Gift from past self: For me, one thing that helped me early on was considering the money I earned in consulting a “gift from my former self.” I’m not sure why this worked so well, but it cracked me up thinking about my spreadsheet self making a presentation telling me why he was investing in my wanderings and creative experiments.

• A self-funded personal MBA: When I took out $70k in debt and went 27 months without working and earning $0, I was seen as successful. But in my first year after quitting my job, I broke even, and people thought I was doing something incredibly risky. Seeing this year as a “personal MBA” helped me get more comfortable with potentially not earning enough money and having to tap into savings.

• New identity: While this is often counterintuitive for people, many people who go through a life change, like having a child, feel an increased urgency to make a change. It used to surprise me how many parents I met who made big changes after having a child, but it makes more sense now. Going through health crises can do the same thing. I know for me, once I recovered from three years of health nonsense, I no longer wanted to waste days at work doing things I didn’t enjoy for people I didn’t respect.

• Off-ramp: A “no-brainer” opportunity can often make the transition smoother, like the potential of moving to a part-time contractor role at your company, or a freelance gig that pays well:

  • commented on the original version of this post that, “For me, it was finding 2 people who were working as freelance consultants in my area of work. I worked under them, they brought me in as a subcontractor on projects, and they mentored me. Seeing up close how their lives worked (and how much free time it opened up), but how they were still earning “good enough” money and were “well respected” made keeping my regular job seem silly.”

• Safety net: Anytime you write about quitting your job, Americans, no matter how much money they have, mention healthcare. It is an awful system we have, but I think it tends to be a default excuse that most people find acceptable rather than a hard and fast reality. Having many ongoing health issues and being uninsured (using Crowdhealth) for two years and on five different state exchanges over the last eight years, it’s not as bad as people think. It does take a little hacking, but Obamacare fixed many of the worst issues. Before Obamacare, many self-employed people couldn’t even buy insurance if they wanted to. Now, you can buy it in every state, and the amount you pay is capped as a % of your income by federal law. Despite this, some people will never leap unless they have coverage through a spouse or some form of part-time gig.

One of the most consistent things I’ve noticed about doing your own thing or taking a break from work is that people feel they need permission. But you can get permission in many different forms. Seeing others do the same thing. Reading a book about someone’s experience. Through unexpected cash injections, or even through a better story that you create.

I’d love to hear other stories or kinds of “leap capital” that inspired people to make a change.

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Heyo, you made it all the way down here

I’ve been doing some form of public writing since 2015. I’ve somehow figured out how to hack a living doing things like writing book,s and next week, launching my own fancy hardcover edition.

If you like what you read here, you’ll probably enjoy my books The Pathless Path and Good Work:

If you’d like to join a virtual community of others on “pathless paths” from around the world, and get access to courses, tools, and other resources I’ve created over the years, you can join The Pathless Path Community. Our recent WhatsApp community is very active if you like hanging out on messaging apps instead of Circle.

Some things I endorse:

• Readwise is offering 2 months free (I use it for book notes and reviewing highlights). Or two months free on

• Readwise Reader, which I use for RSS reading and epub reading

• Crowdhealth, an alternative to US health insurance that I’m still using while abroad

• Postbridge: A social scheduling app created by a reader without crazy upcharges for more accounts

• Kindred, a home-sharing app

• Collective for handling your S-Corp accounting needs; and Nat Eliason’s Build Your Own AI Apps course

If you received this and find yourself in a state of outrage, thinking, “What is this?” I strongly encourage you to unsubscribe below. It is your god given right, and there is plenty of other good stuff online.

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